US20010036479A1 - Glyburide composition - Google Patents
Glyburide composition Download PDFInfo
- Publication number
- US20010036479A1 US20010036479A1 US09/735,334 US73533400A US2001036479A1 US 20010036479 A1 US20010036479 A1 US 20010036479A1 US 73533400 A US73533400 A US 73533400A US 2001036479 A1 US2001036479 A1 US 2001036479A1
- Authority
- US
- United States
- Prior art keywords
- glyburide
- drug
- tablet
- substance
- particle size
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/59—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- the present invention relates to a physical form of the known drug substance glyburide, also known as glibenclamide, and chemically defined as 5-chloro-N-[2-[4-[[[(cyclohexylamino)-carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide (Merck Index, Tenth Edition, p. 642), as well as to dosage forms, e.g., tablets and capsules, incorporating said physical form of glyburide.
- glyburide also known as glibenclamide
- dosage forms e.g., tablets and capsules, incorporating said physical form of glyburide.
- the physical form of glyburide which is the subject matter of this invention is glyburide having a defined particle size distribution.
- This particle size distribution provides an enhanced rate of dissolution of the glyburide compared to bulk glyburide, and it provides reproducible bioavailability in vivo.
- the glyburide of the invention can also be incorporated into a tablet or capsule matrix to enhance the physicochemical (e.g., rate of drug dissolution and absorption) properties desired.
- the preferred rates of dissolution and absorption herein provide for early onset of glyburide absorption, yet avoid the very high and rapidly achieved plasma drug concentrations (“spike”) that would be achieved with prior art formulations when attempting to provide for early onset of absorption.
- the glyburide of the physical form described in this invention achieves this early rate of absorption, yet also maintains exposure of the patient to drug (as measured by the area under the plasma drug concentration against time curve), and therefore maintains the efficacy of the formulation.
- the glyburide of the subject invention and formulations based on this material, have properties that are particularly suitable for use as oral preprandial secretagogues.
- Glyburide of the physical form described in this invention can also be used in formulations combining it with other drugs used in the treatment of type II diabetes.
- examples include, but would not be limited to, acarbose or other glycosidase inhibitors, rosiglitazone, pioglitazone or other thiazolidonediones, biguanides such as metformin fumarate, repaglinide and other “aglinides”.
- Glyburide with the particle size distribution as given in the current invention may be particularly useful in cases where co-formulation with drugs of high dose and high solubility are required.
- An example of such a drug used for the treatment of type II diabetes is the biguanide known as metformin (including its fumarate and hydrochloride salts).
- Glyburide is a commercially available product indicated for the treatment of type II diabetes. Its mode of action is that of an insulin secretagogue, i.e., that of an agent which stimulates the secretion of insulin from patient's beta cells. (See U.S. Pat. Nos. 3,426,067; 3,454,635; 3,507,961 and 3,507,954.) Subsequent to the discovery of glyburide itself, glyburide compositions with enhanced bioavailability to that of the originally developed and marketed formulation became available, for example as described in U.S. Pat. No. 3,979,520 and 4,060,634.
- micronized or high surface area e.g., 3 to 10 m 2 /g
- glyburide in combination with various pharmaceutically acceptable excipients to obtain enhanced bioavailability.
- Another composition in the prior art relates to the use of a spray dried lactose formulation of micronized glyburide having a narrow distribution of particle sizes.
- the spray dried lactose in said composition is the preponderant excipient (not less than 70% of the final composition.)
- U.S. Pat. No. 5,258,185 describes rapidly absorbable formulations of glyburide prepared by dissolving the drug in liquid polyethylene glycol and/or an alcohol (e.g., ethanol) with a sugar alcohol (e.g., sorbitol) solution and optionally an alkalizing agent (e.g., ammonia).
- a sugar alcohol e.g., sorbitol
- an alkalizing agent e.g., ammonia
- Ganley J. Pharm. Pharmac., 36:734-739, 1984
- Shaheen Int. J. Pharm., 38:123-131, 1987
- excipients would be highly soluble in water, and hence dissolve rapidly when the dosage form is immersed in an aqueous environment. In this way, the poorly soluble glyburide is liberated as a finely divided suspension. Dissolution of glyburide from this suspension, the rate of which is controlled by the particle size distribution of the suspension, is a prerequisite for absorption. Hence, the absorption characteristics are defined by the particle size distribution of the glyburide. In this way, as modeled by in vitro testing, the preferred dosage form is rapidly converted to a suspension of glyburide particles when the dosage form is ingested. Poorly soluble excipients may result in a dosage form that erodes too slowly.
- dosage forms prepared with the insoluble excipient dicalcium phospate show slow erosion and consequently slow liberation of glyburide.
- Some currently marketed glyburide formulations, for example MicronaseTM employ such excipients, and as a result can exhibit relatively slow liberation of glyburide into solution.
- the appropriate bioavailability of glyburide avoids rapidly achieving a very high maximum (“spiked”) drug concentration in blood plasma. A very high concentration can predispose the patient to undesirable hypoglycemia. Additionally, the appropriate bioavailability of glyburide provides for the adequate extent of drug absorption such that an area under the plasma drug concentration against time curve maintains efficacy. While not being bound by any theory, it appears that it is this combination, i.e., the early onset of glyburide absorption, without producing excessively high maximum plasma drug concentrations, yet also maintaining exposure of the patient to the drug, that permits the glyburide of this invention to be employed as an oral preprandial secretagogue.
- the particle size measurement method of laser light scattering uses drug substance dispersed in liquid paraffin for introduction into the measurement cell.
- the apparatus produces a volume based, cumulative size distribution. Based on the above data and this methodology, it was found that the preferred particle sizes for glyburide to assure reproducibility of dissolution and bioavailability are:
- Particularly preferred particle sizes for glyburide are:
- Glyburide having these particle size characteristics have powder surface area values in the range of about 1.7 to 2.2 m 2 g ⁇ 1 as determined by nitrogen adsorption. This is yet another difference between the glyburide of the invention and that of the prior art.
- the glyburide of the prior art generally required its powder surface area to be in excess of 3 m 2 g ⁇ 1 (preferably 5 to 10 m 2 g ⁇ 1 ) to yield appropriate glyburide bioavailability.
- the glyburide of particle size properties detailed herein produces appropriate glyburide bioavailability in humans.
- the glyburide When formulating the glyburide into a tablet or capsule, it is preferable to include in the formulation a suitable level of highly water-soluble excipients. Such excipients are generally soluble in water from 50 mg/ml to in excess of 300 mg/ml. They can be used singly or in combination and may comprise 45 to 90% by weight of the total formulation. Such a material used in a tablet or capsule formulation will completely dissolve within 5 to 30 minutes when subjected to an in vitro drug release test procedure, liberating the suspension of glyburide particles.
- the formulation may also include a binder such as povidone or low viscosity hydroxypropyl methylcellulose and a lubricant, such as magnesium stearate or sodium stearyl fumarate.
- a disintegrant has been found to be highly desirable to assure the rapid break up of the dosage form when immersed in an aqueous environment.
- Suitable disintegrants include croscarmellose sodium or sodium starch glycollate.
- the formulation may optionally include other excipients such as glidants, anti-adherents, colors, flavors, film coating components (including polymers such as hydroxypropyl methylcellulose, wetting agents such as polysorbate 20, plasticizers such as polyethylene glycol 200), and other materials commonly used in the formulation of tablets and capsules and as would be familiar to those skilled in the art.
- Suitable highly water soluble excipients would also include, but not be limited to, sugar alcohols such as mannitol, sorbitol and xylitol; sugars such as sucrose, lactose, maltose and glucose; oligosaccharides such as maltodextrins.
- the glyburide was blended with the croscarmellose sodium and that mixture was blended with the mannitol.
- the resulting blend was wet granulated using the povidone dissolved in an appropriate amount of purified water.
- the granules obtained were dried to an appropriate residual moisture content, mixed with the microcrystalline cellulose, lubricated by mixing with the magnesium stearate and compressed into tablets each containing 5 mg of glyburide.
- the tablets were subjected to an in vitro dissolution method to determine the rate at which the glyburide was released from the tablets.
- the tablets were placed into a dissolution medium of pH 6.4 phosphate buffer with 1% w/w sodium dodecyl sulphate, and stirred with paddles at 50 rpm. It was found that 80% of the drug in the tablet was dissolved within 20 minutes.
- a process similar to the process described in Example 2 would yield tablets containing 1.25 mg of glyburide.
- the tablets are optionally film coated with a proprietary film coat composition such as OPADRY, employing a side vented coating pan.
- the glyburide of the invention can be co-formulated with other drugs for the treatment of type II diabetes. This would facilitate treatment for patients having to take multiple medications when single drug therapy is inadequate to control their disease.
- agents might include, but would not be limited to, acarbose or other glycosidase inhibitors, rosiglitazone, pioglitazone or other thiazolidonediones, biguanides such as metformin fumarate, repaglinide and other “aglinides”.
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/735,334 US20010036479A1 (en) | 2000-01-14 | 2000-12-11 | Glyburide composition |
US10/426,211 US6830760B2 (en) | 2000-01-14 | 2003-04-30 | Glyburide composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US48370300A | 2000-01-14 | 2000-01-14 | |
US09/735,334 US20010036479A1 (en) | 2000-01-14 | 2000-12-11 | Glyburide composition |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US48370300A Continuation-In-Part | 2000-01-14 | 2000-01-14 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/426,211 Continuation US6830760B2 (en) | 2000-01-14 | 2003-04-30 | Glyburide composition |
Publications (1)
Publication Number | Publication Date |
---|---|
US20010036479A1 true US20010036479A1 (en) | 2001-11-01 |
Family
ID=23921174
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/735,334 Abandoned US20010036479A1 (en) | 2000-01-14 | 2000-12-11 | Glyburide composition |
US10/426,211 Expired - Lifetime US6830760B2 (en) | 2000-01-14 | 2003-04-30 | Glyburide composition |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/426,211 Expired - Lifetime US6830760B2 (en) | 2000-01-14 | 2003-04-30 | Glyburide composition |
Country Status (37)
Country | Link |
---|---|
US (2) | US20010036479A1 (ko) |
EP (1) | EP1250321B1 (ko) |
JP (1) | JP4787446B2 (ko) |
KR (1) | KR100739906B1 (ko) |
CN (1) | CN1210258C (ko) |
AR (1) | AR031547A1 (ko) |
AT (1) | ATE330937T1 (ko) |
AU (1) | AU771705B2 (ko) |
BG (1) | BG65782B1 (ko) |
BR (1) | BR0107564A (ko) |
CA (1) | CA2397294C (ko) |
CY (1) | CY1106328T1 (ko) |
CZ (1) | CZ20022429A3 (ko) |
DE (1) | DE60120916T2 (ko) |
DK (1) | DK1250321T3 (ko) |
EE (1) | EE05020B1 (ko) |
ES (1) | ES2264967T3 (ko) |
GE (1) | GEP20043299B (ko) |
HU (1) | HU228825B1 (ko) |
IL (2) | IL150383A0 (ko) |
LT (1) | LT5024B (ko) |
LV (1) | LV12914B (ko) |
MX (1) | MXPA02006835A (ko) |
MY (1) | MY128577A (ko) |
NO (1) | NO328152B1 (ko) |
NZ (1) | NZ519920A (ko) |
PT (1) | PT1250321E (ko) |
RO (1) | RO121381B1 (ko) |
RU (1) | RU2244707C2 (ko) |
SK (1) | SK286925B6 (ko) |
TN (1) | TNSN01005A1 (ko) |
TR (1) | TR200201798T2 (ko) |
TW (1) | TWI287989B (ko) |
UA (1) | UA73968C2 (ko) |
UY (1) | UY26529A1 (ko) |
WO (1) | WO2001051463A1 (ko) |
ZA (1) | ZA200205528B (ko) |
Cited By (2)
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---|---|---|---|---|
WO2007131930A1 (en) * | 2006-05-13 | 2007-11-22 | Novo Nordisk A/S | Tablet formulation comprising repaglinide and metformin |
US8911781B2 (en) | 2002-06-17 | 2014-12-16 | Inventia Healthcare Private Limited | Process of manufacture of novel drug delivery system: multilayer tablet composition of thiazolidinedione and biguanides |
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US7767249B2 (en) * | 2001-06-07 | 2010-08-03 | Hewlett-Packard Development Company, L.P. | Preparation of nanoparticles |
US20050271737A1 (en) * | 2001-06-07 | 2005-12-08 | Chinea Vanessa I | Application of a bioactive agent to a substrate |
EP1465628A2 (en) * | 2002-03-21 | 2004-10-13 | Teva Pharmaceutical Industries Ltd. | Fine particle size pioglitazone |
RU2359661C2 (ru) | 2003-10-31 | 2009-06-27 | Такеда Фармасьютикал Компани Лимитед | Твердый препарат |
CA2563325C (en) * | 2004-04-29 | 2010-06-22 | Lotus Pharmaceutical Co., Ltd. | Oral modified-release lozenges and their preparation method |
CN100455279C (zh) * | 2004-04-29 | 2009-01-28 | 美时化学制药股份有限公司 | 口服延迟释放锭剂组成物及其制法 |
CN100341495C (zh) * | 2004-12-29 | 2007-10-10 | 三九医药股份有限公司 | 格列本脲固体分散体、口服组合物及其制备方法 |
WO2006109175A2 (en) * | 2005-04-11 | 2006-10-19 | Aurobindo Pharma Limited | Solid dosage form of an antidiabetic drug |
US8529537B2 (en) * | 2005-08-05 | 2013-09-10 | Kimberly-Clark Worldwide, Inc. | Absorbent article with enclosures |
CN101287467B (zh) * | 2005-08-22 | 2011-01-19 | 梅里奥尔医药I公司 | 用于调节Lyn激酶活性和治疗相关病症的方法和制剂 |
US7776870B2 (en) | 2005-08-22 | 2010-08-17 | Melior Pharmaceuticals I, Inc. | Methods for modulating Lyn kinase activity and treating related disorders |
TW200816995A (en) * | 2006-08-31 | 2008-04-16 | Daiichi Sankyo Co Ltd | Pharmaceutical composition containing insulin sensitizers |
EP1967182A1 (en) * | 2007-03-07 | 2008-09-10 | KRKA, tovarna zdravil, d.d., Novo mesto | Pharmaceutical composition comprising a salt of rosigliatazone |
US8552184B2 (en) | 2008-07-03 | 2013-10-08 | Melior Pharmaceuticals I, Inc. | Compounds and methods for treating disorders related to glucose metabolism |
WO2010048287A2 (en) | 2008-10-22 | 2010-04-29 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Radioprotective agents |
US20130158055A1 (en) | 2010-05-28 | 2013-06-20 | Andrew G. Reaume | Prevention Of Pancreatic Beta Cell Degeneration |
EP2520298A1 (en) | 2011-05-03 | 2012-11-07 | Assistance Publique, Hopitaux De Paris | Pharmaceutical composition comprising sulfonylureas (glibenclamide) or meglitinides for use for treating hyperglycaemia or for promoting growth of a premature infant |
CN102743354A (zh) * | 2012-07-31 | 2012-10-24 | 南京正科制药有限公司 | 瑞格列奈片及其制备方法 |
CN103142521B (zh) * | 2013-03-21 | 2014-06-25 | 西南药业股份有限公司 | 格列本脲片及其制备方法 |
CN104127423A (zh) * | 2014-07-30 | 2014-11-05 | 沈阳药科大学 | 格列喹酮衍生物及其制备方法和应用 |
CN104127424A (zh) * | 2014-07-30 | 2014-11-05 | 沈阳药科大学 | 格列本脲衍生物及其制备方法和应用 |
JP7182605B2 (ja) | 2017-04-10 | 2022-12-02 | メリオール・ファーマスーティカルズ・ワン・インコーポレイテッド | lynキナーゼ活性化因子及びTRPM8アゴニストを含む組成物及び医薬の製造におけるそれらの使用 |
CN113143940A (zh) * | 2020-12-30 | 2021-07-23 | 成都恒瑞制药有限公司 | 一种抗糖尿病药物组合物的制备方法 |
WO2023012610A1 (en) * | 2021-08-03 | 2023-02-09 | Avaca Pharma Private Limited | Formulations, compositions and methods for the treatment of stroke |
Citations (10)
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US3174901A (en) * | 1963-01-31 | 1965-03-23 | Jan Marcel Didier Aron Samuel | Process for the oral treatment of diabetes |
US3979520A (en) * | 1973-09-26 | 1976-09-07 | Boehringer Mannheim G.M.B.H. | Preparation of rapidly resorbable glibenclamide |
US4060634A (en) * | 1973-09-26 | 1977-11-29 | Boehringer Mannheim G.M.B.H. | Rapidly resorbable glibenclamide |
US4916163A (en) * | 1985-06-04 | 1990-04-10 | The Upjohn Company | Spray-dried lactose formulation of micronized glyburide |
US5631224A (en) * | 1992-03-19 | 1997-05-20 | Novo Nordisk A/S | Use of a peptide |
US5663198A (en) * | 1993-07-15 | 1997-09-02 | Hoechst Aktiengesellschaft | Drug formulations comprising coated, very sparingly water-soluble drugs for inhalational pharmaceutical forms, and process for their preparation |
US5922769A (en) * | 1995-11-14 | 1999-07-13 | Abiogen Pharma S.R.L. | Glibenclamide-metformin combination for the treatment of diabetes mellitus of type II |
US5932245A (en) * | 1991-12-05 | 1999-08-03 | Alfatec Pharma Gmbh | Gelatin or collagen hydrolysate containing drug formulation that provides for immediate release of nanoparticle drug compounds |
US5965584A (en) * | 1995-06-20 | 1999-10-12 | Takeda Chemical Industries, Ltd. | Pharmaceutical composition |
US6153632A (en) * | 1997-02-24 | 2000-11-28 | Rieveley; Robert B. | Method and composition for the treatment of diabetes |
Family Cites Families (13)
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DE1185180B (de) | 1963-10-19 | 1965-01-14 | Hoechst Ag | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
US3454635A (en) | 1965-07-27 | 1969-07-08 | Hoechst Ag | Benzenesulfonyl-ureas and process for their manufacture |
CA889876A (en) | 1970-09-10 | 1972-01-04 | Frank W. Horner Limited | Purification of glyburide |
DE3833439A1 (de) | 1988-10-01 | 1991-09-12 | Hoechst Ag | Verfahren zur mikronisierung von glibenclamid |
RU2026670C1 (ru) | 1988-10-05 | 1995-01-20 | Дзе Апджон Компани | Способ получения тонкодисперсного твердого фармацевтического вещества |
US5258185A (en) | 1989-08-23 | 1993-11-02 | Bauer Kurt H | Highly active, rapidly absorbable formulations of glibenclamide, processes for the production thereof and their use |
DE19721467A1 (de) * | 1997-05-22 | 1998-11-26 | Basf Ag | Verfahren zur Herstellung kleinteiliger Zubereitungen biologisch aktiver Stoffe |
ATE355840T1 (de) | 1997-06-18 | 2007-03-15 | Smithkline Beecham Plc | Behandlung der diabetes mit thiazolidindione und metformin |
GB9715306D0 (en) | 1997-07-18 | 1997-09-24 | Smithkline Beecham Plc | Novel method of treatment |
WO1999021534A1 (en) * | 1997-10-27 | 1999-05-06 | Merck Patent Gmbh | Solid state solutions and dispersions of poorly water soluble drugs |
PT974356E (pt) | 1998-07-15 | 2004-02-27 | Merck Sante Sas | Comprimidos compreendendo uma combinacao de metformina e de glibenclamida |
US7374779B2 (en) * | 1999-02-26 | 2008-05-20 | Lipocine, Inc. | Pharmaceutical formulations and systems for improved absorption and multistage release of active agents |
US6294192B1 (en) * | 1999-02-26 | 2001-09-25 | Lipocine, Inc. | Triglyceride-free compositions and methods for improved delivery of hydrophobic therapeutic agents |
-
2000
- 2000-12-11 US US09/735,334 patent/US20010036479A1/en not_active Abandoned
- 2000-12-20 MY MYPI20005969A patent/MY128577A/en unknown
-
2001
- 2001-01-04 RU RU2002121626/04A patent/RU2244707C2/ru active
- 2001-01-04 DE DE60120916T patent/DE60120916T2/de not_active Expired - Lifetime
- 2001-01-04 ES ES01900328T patent/ES2264967T3/es not_active Expired - Lifetime
- 2001-01-04 EP EP01900328A patent/EP1250321B1/en not_active Expired - Lifetime
- 2001-01-04 DK DK01900328T patent/DK1250321T3/da active
- 2001-01-04 RO ROA200200979A patent/RO121381B1/ro unknown
- 2001-01-04 TR TR2002/01798T patent/TR200201798T2/xx unknown
- 2001-01-04 SK SK983-2002A patent/SK286925B6/sk not_active IP Right Cessation
- 2001-01-04 PT PT01900328T patent/PT1250321E/pt unknown
- 2001-01-04 CA CA2397294A patent/CA2397294C/en not_active Expired - Lifetime
- 2001-01-04 AU AU24740/01A patent/AU771705B2/en not_active Expired
- 2001-01-04 NZ NZ519920A patent/NZ519920A/en not_active IP Right Cessation
- 2001-01-04 CN CNB018036392A patent/CN1210258C/zh not_active Expired - Lifetime
- 2001-01-04 AT AT01900328T patent/ATE330937T1/de active
- 2001-01-04 KR KR1020027009084A patent/KR100739906B1/ko active IP Right Grant
- 2001-01-04 BR BR0107564-0A patent/BR0107564A/pt not_active Application Discontinuation
- 2001-01-04 GE GE4874A patent/GEP20043299B/en unknown
- 2001-01-04 HU HU0203852A patent/HU228825B1/hu unknown
- 2001-01-04 EE EEP200200393A patent/EE05020B1/xx unknown
- 2001-01-04 CZ CZ20022429A patent/CZ20022429A3/cs unknown
- 2001-01-04 IL IL15038301A patent/IL150383A0/xx active IP Right Grant
- 2001-01-04 JP JP2001551845A patent/JP4787446B2/ja not_active Expired - Lifetime
- 2001-01-04 MX MXPA02006835A patent/MXPA02006835A/es active IP Right Grant
- 2001-01-04 WO PCT/US2001/000234 patent/WO2001051463A1/en active IP Right Grant
- 2001-01-08 TW TW090100369A patent/TWI287989B/zh not_active IP Right Cessation
- 2001-01-11 TN TNTNSN01005A patent/TNSN01005A1/en unknown
- 2001-01-11 UY UY26529A patent/UY26529A1/es not_active Application Discontinuation
- 2001-01-12 AR ARP010100161A patent/AR031547A1/es not_active Application Discontinuation
- 2001-04-01 UA UA2002086718A patent/UA73968C2/uk unknown
-
2002
- 2002-06-24 BG BG106870A patent/BG65782B1/bg unknown
- 2002-06-24 IL IL150383A patent/IL150383A/en unknown
- 2002-07-10 ZA ZA200205528A patent/ZA200205528B/xx unknown
- 2002-07-12 NO NO20023367A patent/NO328152B1/no not_active IP Right Cessation
- 2002-07-23 LT LT2002085A patent/LT5024B/lt not_active IP Right Cessation
- 2002-08-09 LV LVP-02-144A patent/LV12914B/en unknown
-
2003
- 2003-04-30 US US10/426,211 patent/US6830760B2/en not_active Expired - Lifetime
-
2006
- 2006-09-20 CY CY20061101349T patent/CY1106328T1/el unknown
Patent Citations (10)
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US3174901A (en) * | 1963-01-31 | 1965-03-23 | Jan Marcel Didier Aron Samuel | Process for the oral treatment of diabetes |
US3979520A (en) * | 1973-09-26 | 1976-09-07 | Boehringer Mannheim G.M.B.H. | Preparation of rapidly resorbable glibenclamide |
US4060634A (en) * | 1973-09-26 | 1977-11-29 | Boehringer Mannheim G.M.B.H. | Rapidly resorbable glibenclamide |
US4916163A (en) * | 1985-06-04 | 1990-04-10 | The Upjohn Company | Spray-dried lactose formulation of micronized glyburide |
US5932245A (en) * | 1991-12-05 | 1999-08-03 | Alfatec Pharma Gmbh | Gelatin or collagen hydrolysate containing drug formulation that provides for immediate release of nanoparticle drug compounds |
US5631224A (en) * | 1992-03-19 | 1997-05-20 | Novo Nordisk A/S | Use of a peptide |
US5663198A (en) * | 1993-07-15 | 1997-09-02 | Hoechst Aktiengesellschaft | Drug formulations comprising coated, very sparingly water-soluble drugs for inhalational pharmaceutical forms, and process for their preparation |
US5965584A (en) * | 1995-06-20 | 1999-10-12 | Takeda Chemical Industries, Ltd. | Pharmaceutical composition |
US5922769A (en) * | 1995-11-14 | 1999-07-13 | Abiogen Pharma S.R.L. | Glibenclamide-metformin combination for the treatment of diabetes mellitus of type II |
US6153632A (en) * | 1997-02-24 | 2000-11-28 | Rieveley; Robert B. | Method and composition for the treatment of diabetes |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8911781B2 (en) | 2002-06-17 | 2014-12-16 | Inventia Healthcare Private Limited | Process of manufacture of novel drug delivery system: multilayer tablet composition of thiazolidinedione and biguanides |
WO2007131930A1 (en) * | 2006-05-13 | 2007-11-22 | Novo Nordisk A/S | Tablet formulation comprising repaglinide and metformin |
US20090252790A1 (en) * | 2006-05-13 | 2009-10-08 | Novo Nordisk A/S | Tablet formulation |
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