WO2013005226A1 - A novel combined pharmaceutical composition containing diclofenac and methods of making and using the same - Google Patents
A novel combined pharmaceutical composition containing diclofenac and methods of making and using the same Download PDFInfo
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- WO2013005226A1 WO2013005226A1 PCT/IN2011/000868 IN2011000868W WO2013005226A1 WO 2013005226 A1 WO2013005226 A1 WO 2013005226A1 IN 2011000868 W IN2011000868 W IN 2011000868W WO 2013005226 A1 WO2013005226 A1 WO 2013005226A1
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- pharmaceutical composition
- drotaverine
- pain
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- diclofenac
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- 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
-
- 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
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
-
- 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]
Definitions
- the present combined pharmaceutical composition relates to the synergistic pharmaceutical composition more preferably an oral and injectable administration of optimized, high bioavailability formulation of the active ingredient which typically is diclofenac, glycofurol and Drotaverine with the pharmaceutically accepted excipients.
- Drotaverine (INN, also known as drotaverin) is an antispasmodic drug, structurally related to papaverine. Drotaverine is a selective inhibitor of phosphodiesterase 4, and has no anticholinergic effects. Drotaverine has been shown to possess dose-dependant analgesic effects in animal models.
- Drotaverine has been shown to be effective in paracervical block in managing pain during hysteroscopy and endometrial biopsy when administered together with mefenamic acid. Drotaverin has also been tested in combination with rimantadine for antiviral activity against A and B type influenza.
- Drotaverine is sold under brand name No-Spa (Chinoin Pharmaceutical and Chemical Works, Hungary, a member of the Sanofi-Aventis.
- Diclofenac (marketed under many brand names, see below: Trade names) is a non-steroidal anti-inflammatory drug (NSAID) taken to reduce inflammation and as an analgesic reducing pain in certain conditions.
- NSAID non-steroidal anti-inflammatory drug
- the name is derived from its chemical name: 2-(2,6- dichloranilino) phenylacetic acid. In the United Kingdom, India, Brazil and the United States, it may be supplied as either the sodium or potassium salt, in China most often as the sodium salt, while in some other countries only as the potassium salt.
- Diclofenac is available as a generic drug in a number of formulations. Over the counter (OTC) use is approved in some countries for minor aches and pains and fever associated with common infections.
- compositions described herein are methods of using the compositions described herein to overcome polymorphism, overcome solubility and delivery problems, to control release rates, add functionality, enhance efficacy (synergy), and improve ease of use and manufacture.
- the present invention relates to a novel chemical process that provides novel vehicle derivatives that are exceptional 1,2- or 1,3-aminothiol specific reagents for conjugation to unprotected targeted compounds (e.g., polypeptides, peptides, or organic compounds) having or modified to have a 1,2- or 1,3 aminothiol group.
- unprotected targeted compounds e.g., polypeptides, peptides, or organic compounds
- the invention further relates to the methods of using novel water-soluble polymer derivatives and conjugates thereof.
- An injectable formulation containing a soluble salt of clavulanic acid and a soluble salt of an .alpha. -aminopenicillin or cephalosporin has its stability on reconstitution improved by the incorporation therein of glycofurol.
- An object of the present invention is to solve the problem of dry mouth with difficulty in swallowing and thirst, dilatation of pupils with loss of accommodation and sensitivity to light, increased intraocular pressure, flushing, dry skin, bradycardia followed by tachycardia, palpitation and arrhythmia, difficulty with micturition; rarely fever, confusional states and rashes, Contraindicated in closed angle glaucoma
- An object of the present combined pharmaceutical composition is to provide caution free treatment for patients who suffered from tachycardia, cardiac insufficiency ,urinary retention , prostatic hypertrophy, paralytic ileus, ulcerative colitis, pyloric stenosis; may aggravate gastroesophageal reflex ,during pregnancy , blurring of vision, vomiting, palpitation, nervousness, giddiness, blurred vision ,drug-rash, urinary retention, palpitation and fetal tachycardia thereof.
- An object of the present invention is to prevent from Anticholinergic side effects.
- IV administration may lead to increased pulse rate, vision disturbances, Prostate hypertrophy with urinary retention, megacolon, Gl mechanical stenosis and tachycardia thereof.
- An object of the present invention is to providing sufficient dosage.
- a further object of the present invention is to demonstrate improved stability, solubility characteristics and enhanced appearance compared with currently available compositions.
- An additional object of the present invention is to decrease the reconstitution time.
- An object of the present invention is to provide the formulation which gives an established, reliable, and accepted and comparatively smooth yet Speedy Recovery.
- An object of the present invention is to provide the composition with the Drotaverine and Diclofenac which are well tolerated. Skin rashes, diarrhea, dyspepsia have been reported with Diclofenac in few patients when it is used alone.
- An object of the present invention is to provide the formulation which is free from anti cholinergic side effects like blurring of vision and dryness of mouth. Hence, it can be administered to patients with glaucoma or benign prostatic hyperplasia where antispasmodics are contraindicated.
- the present invention refers to combined pharmaceutical composition comprises diclofenac, drotaverine and glycofurol with the pharmaceutically accepted excipients.
- Drotaverine which is a musculotropic drug acting directly on smooth muscle cells.
- Drotaverine has a dual mechanism of action. Drotaverine inhibits the ertzyme phosphodiesterase IV (PDE IV).
- cAMP cyclic adenosine monophosphate level
- Ca2+ free calcium ions
- CM-Ca2+ Calmodulin-Calcium Complex
- the onset of action of Drotaverine on oral administration is about 12 minutes and injectable form is very quick and it's safe in all kind of administration.
- Drotaverine rapidly penetrates into the organs after oral administration.
- the main advantage of this combination is that, the route of administration of Drotaverine does not influence its metabolism.
- the metabolite of Drotaverine is 4'-desethyl- drotaveraldine.
- the metabolites are inactive and the spasmolytic effect is exerted by the unchanged drug in the body.
- the Colic is the term that refers to the pain produced by obstruction or spasm of hollow abdominal organs such as:-
- dysmenorrhea which is one of the most common gynecological disease. It is classified as primary and secondary dysmenorrhea.
- Glycofurol which is used as solvent to dissolve water-insoluble compounds. It is stable but combustible and incompatible with strong oxidizing agents. The main unique feature of this ingredient is less painful, water soluble, less irritant, better bio availability, high effectiveness and ready to use. It has been reported to be non-toxic and non- irritating when diluted in water.
- Glycofurol also called tetrahydrofurane is a substance available on the market with the empiric formula (C2H40) XC4H802, in which X is about 2. This substance is well mixable with water and soluble in ether, ethanol, propanol and glycerol and has a low toxicity.
- diclofenac i.e. 2-[(2,6-dichlorophenyl)amino]benzene acetic acid monosodium salt
- diclofenac i.e. 2-[(2,6-dichlorophenyl)amino]benzene acetic acid monosodium salt
- Diclofenac acts by inhibiting the synthesis of prostaglandins, the principal cause of inflammation and pain. To achieve the maximum effectiveness in pain relief the active principle must reach the systemic circulation as soon as possible after administration, so consequently the injectable form has always been favoured particularly for the treatment of acute inflammations of the musculoskeletal system. Diclofenac is used to treat pain, inflammatory disorders, and dysmenorrhea.
- Inflammatory disorder may include musculoskeletal complaints, especially arthritis, rheumatoid arthritis, polymyositis, dermatomyositis, osteoarthritis, dental pain, TMJ, spondylarthritis, ankylosing spondylitis, gout attacks, and pain management in cases of kidney stones and gallstones.
- An additional indication is the treatment of acute migraines.
- Diclofenac is used commonly to treat mild to moderate post-operative or post-traumatic pain, particularly when inflammation is also present, and is effective against menstrual pain and endometriosis.
- diclofenac Mechanism of diclofenac is a unique member of the NSAIDs. There is some evidence that diclofenac inhibits the lipoxygenase pathways, thus reducing formation of the leukotrienes (also pro-inflammatory autacoids). There is also speculation that diclofenac may inhibit phospholipase A2 as part of its mechanism of action. These additional actions may explain the high potency of diclofenac - it is the most potent NSAID on a broad basis.
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- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Abstract
The present invention related to a synergistic pharmaceutical composition which contains more than one active ingredients which are diclofenac, glycofurol and Drotaverine with pharmaceutically accepted excipients. The present stable and effective combined composition shows enhanced efficacy and synergistic effect to provide protection from Dysmenorrhea, Gastrointestinal colic, Biliary colic, Renal colic, Dysmenorrheal and Abdominal pain associated with irritable bowel syndrome, Pre and Post lithotripsy, Post surgical smooth muscle spasm, Post-MTP (Medical termination of pregnancy) and D&C Dilatation and curettage thereof.
Description
A NOVEL COMBINED PHARMACEUTICAL COMPOSITION CONTAINING DICLOFENAC AND METHODS OF MAKING AND USING THE SAME
FIELD OF THE I VENTION-
The present combined pharmaceutical composition relates to the synergistic pharmaceutical composition more preferably an oral and injectable administration of optimized, high bioavailability formulation of the active ingredient which typically is diclofenac, glycofurol and Drotaverine with the pharmaceutically accepted excipients.
BACKGROUND AND PRIOR ART-
Drotaverine (INN, also known as drotaverin) is an antispasmodic drug, structurally related to papaverine. Drotaverine is a selective inhibitor of phosphodiesterase 4, and has no anticholinergic effects. Drotaverine has been shown to possess dose-dependant analgesic effects in animal models.
Drotaverine has been shown to be effective in paracervical block in managing pain during hysteroscopy and endometrial biopsy when administered together with mefenamic acid. Drotaverin has also been tested in combination with rimantadine for antiviral activity against A and B type influenza.
Drotaverine is sold under brand name No-Spa (Chinoin Pharmaceutical and Chemical Works, Hungary, a member of the Sanofi-Aventis.
Diclofenac (marketed under many brand names, see below: Trade names) is a non-steroidal anti-inflammatory drug (NSAID) taken to reduce inflammation and as an analgesic reducing pain in certain conditions. The name is derived from its chemical name: 2-(2,6- dichloranilino) phenylacetic acid.
In the United Kingdom, India, Brazil and the United States, it may be supplied as either the sodium or potassium salt, in China most often as the sodium salt, while in some other countries only as the potassium salt. Diclofenac is available as a generic drug in a number of formulations. Over the counter (OTC) use is approved in some countries for minor aches and pains and fever associated with common infections.
According to United States Patent Application 20070093462 /WO 2007/044693 A 2 wherein Disclosed are ionic liquids and methods of preparing ionic liquid compositions of active pharmaceutical, biological, nutritional, and energetic ingredients.
Also disclosed are methods of using the compositions described herein to overcome polymorphism, overcome solubility and delivery problems, to control release rates, add functionality, enhance efficacy (synergy), and improve ease of use and manufacture.
According to WO/2006/079099/AU 2006/206166 A 1 wherein The present invention relates to a novel chemical process that provides novel vehicle derivatives that are exceptional 1,2- or 1,3-aminothiol specific reagents for conjugation to unprotected targeted compounds (e.g., polypeptides, peptides, or organic compounds) having or modified to have a 1,2- or 1,3 aminothiol group. The invention further relates to the methods of using novel water-soluble polymer derivatives and conjugates thereof.
However there is no formulation or composition of diclofenac, glycofurol and Drotaverine as a synergistic composition with optimized stability and less reconstitution time.
According to a Chinese patent CA Patent 1183454, An injectable formulation containing a soluble salt of clavulanic acid and a soluble salt of an .alpha. -aminopenicillin or cephalosporin has its stability on reconstitution improved by the incorporation therein of glycofurol.
SUMMARY OF THE INVENTION
An object of the present invention is to solve the problem of dry mouth with difficulty in swallowing and thirst, dilatation of pupils with loss of accommodation and sensitivity to light, increased intraocular pressure, flushing, dry skin, bradycardia followed by tachycardia, palpitation and arrhythmia, difficulty with micturition; rarely fever, confusional states and
rashes, Contraindicated in closed angle glaucoma
An object of the present combined pharmaceutical composition is to provide caution free treatment for patients who suffered from tachycardia, cardiac insufficiency ,urinary retention , prostatic hypertrophy, paralytic ileus, ulcerative colitis, pyloric stenosis; may aggravate gastroesophageal reflex ,during pregnancy , blurring of vision, vomiting, palpitation, nervousness, giddiness, blurred vision ,drug-rash, urinary retention, palpitation and fetal tachycardia thereof.
An object of the present invention is to prevent from Anticholinergic side effects. IV administration may lead to increased pulse rate, vision disturbances, Prostate hypertrophy with urinary retention, megacolon, Gl mechanical stenosis and tachycardia thereof.
An object of the present invention is to providing sufficient dosage.
A further object of the present invention is to demonstrate improved stability, solubility characteristics and enhanced appearance compared with currently available compositions.
An additional object of the present invention is to decrease the reconstitution time.
An object of the present invention is to provide the formulation which gives an established, reliable, and accepted and comparatively smooth yet Speedy Recovery.
An object of the present invention is to provide the composition with the Drotaverine and Diclofenac which are well tolerated. Skin rashes, diarrhea, dyspepsia have been reported with Diclofenac in few patients when it is used alone.
An object of the present invention is to provide the formulation which is free from anti cholinergic side effects like blurring of vision and dryness of mouth. Hence, it can be administered to patients with glaucoma or benign prostatic hyperplasia where antispasmodics are contraindicated.
DETAILED DESCRIPTION OF THE INVENTION
The present invention refers to combined pharmaceutical composition comprises diclofenac, drotaverine and glycofurol with the pharmaceutically accepted excipients.
According to a particularly preferred embodiment of the present pharmaceutical composition comprising Drotaverine which is a musculotropic drug acting directly on smooth muscle cells. Drotaverine has a dual mechanism of action. Drotaverine inhibits the ertzyme phosphodiesterase IV (PDE IV).
This cause an increase in cyclic adenosine monophosphate level (cAMP), which results in decrease in concentration of free calcium ions (Ca2+). This process inhibits myosin light chain kinase (MLCK) leading to the dephosphorylation of actomyosin phosphate complex thus causing relaxation of smooth muscles.
Simultaneously Drotaverine inhibits calmodulin (CM). The decrease in Ca2+ ions along with the inhibition of CM leads to the inhibition of "Calmodulin-Calcium Complex" (CM-Ca2+) formation. Drotaverine is well and quickly absorbed from jejunum and ileum. The peak plasma concentration reaches between 45-60 minutes. Half-life of absorption of Drotaverine is 12 minutes.
The onset of action of Drotaverine on oral administration is about 12 minutes and injectable form is very quick and it's safe in all kind of administration.
Drotaverine rapidly penetrates into the organs after oral administration. The peak concentration of the drug in lungs, kidney etc, appears in half a minute and after the injection proving very rapid distribution of the drug.
The main advantage of this combination is that, the route of administration of Drotaverine does not influence its metabolism. The metabolite of Drotaverine is 4'-desethyl- drotaveraldine. The metabolites are inactive and the spasmolytic effect is exerted by the unchanged drug in the body.
It shows enhanced efficacy for the treatment of some diseases which are Gastrointestinal colic, Biliary colic, Renal colic, Dysmenorrhea, Abdominal pain associated with irritable bowel syndrome, Pre and Post lithotripsy, Post surgical smooth muscle spasm, Post-MTP (
Medical termination of pregnancy) and D&C (Dilatation and curettage)
The Colic is the term that refers to the pain produced by obstruction or spasm of hollow abdominal organs such as:-
Gall Bladder and Bile Ducts - Biliary Colic
Ureter - Ureteric Colic
Stomach / small / large intestine - GI Colic thereof
Its useful for the treatment of dysmenorrhea , which is one of the most common gynecological disease. It is classified as primary and secondary dysmenorrhea.
Another active ingredient is Glycofurol which is used as solvent to dissolve water-insoluble compounds. It is stable but combustible and incompatible with strong oxidizing agents. The main unique feature of this ingredient is less painful, water soluble, less irritant, better bio availability, high effectiveness and ready to use. It has been reported to be non-toxic and non- irritating when diluted in water.
Glycofurol, also called tetrahydrofurane is a substance available on the market with the empiric formula (C2H40) XC4H802, in which X is about 2. This substance is well mixable with water and soluble in ether, ethanol, propanol and glycerol and has a low toxicity.
According to a particularly preferred embodiment of the present pharmaceutical composition comprising diclofenac i.e. 2-[(2,6-dichlorophenyl)amino]benzene acetic acid monosodium salt, has a recognised anti-inflammatory activity and for this reason has long been used as the active principle in various types of pharmaceutical formulations used in treating painful conditions, including post-traumatic and post-operative, and in all rheumatic diseases.
Diclofenac acts by inhibiting the synthesis of prostaglandins, the principal cause of inflammation and pain. To achieve the maximum effectiveness in pain relief the active principle must reach the systemic circulation as soon as possible after administration, so consequently the injectable form has always been favoured particularly for the treatment of acute inflammations of the musculoskeletal system.
Diclofenac is used to treat pain, inflammatory disorders, and dysmenorrhea. Inflammatory disorder may include musculoskeletal complaints, especially arthritis, rheumatoid arthritis, polymyositis, dermatomyositis, osteoarthritis, dental pain, TMJ, spondylarthritis, ankylosing spondylitis, gout attacks, and pain management in cases of kidney stones and gallstones. An additional indication is the treatment of acute migraines. Diclofenac is used commonly to treat mild to moderate post-operative or post-traumatic pain, particularly when inflammation is also present, and is effective against menstrual pain and endometriosis.
As long-term use of diclofenac and similar NSAIDs predisposes for peptic ulcer, many patients at risk for this complication are prescribed a combination (Arthrotec) of diclofenac and misoprostol, a synthetic prostaglandin analogue, to protect the gastric mucosa.
Mechanism of diclofenac is a unique member of the NSAIDs. There is some evidence that diclofenac inhibits the lipoxygenase pathways, thus reducing formation of the leukotrienes (also pro-inflammatory autacoids). There is also speculation that diclofenac may inhibit phospholipase A2 as part of its mechanism of action. These additional actions may explain the high potency of diclofenac - it is the most potent NSAID on a broad basis.
Claims
1. A novel combined pharmaceutical composition comprises diclofenac, glycofurol and Drotaverine with pharmaceutically accepted excipients.
2. A novel combined pharmaceutical composition as recited in Claim 1 wherein said it's stable and effective combined composition shows enhanced efficacy and synergistic effect to provide protection from Dysmenorrhea, Gastrointestinal colic, Biliary colic, Renal colic, Dysmenorrheal and Abdominal pain associated with irritable bowel syndrome, Pre and Post lithotripsy, Post surgical smooth muscle spasm, Post-MTP (Medical termination of pregnancy) and D&C Dilatation and curettage thereof
3. A novel combined pharmaceutical composition as recited in Claim 1 wherein said Diclofenac acts by inhibiting the synthesis of prostaglandins, the principal cause of inflammation and pain. To achieve the maximum effectiveness in pain relief the active principle must reach the systemic circulation as soon as possible after administration, so consequently the injectable form has always been favoured particularly for the treatment of acute inflammations of the musculoskeletal system.
4. A novel combined pharmaceutical composition as recited in Claim 3 wherein said Diclofenac is used to treat pain, inflammatory disorders, and dysmenorrhea. Inflammatory disorders may include musculoskeletal complaints, especially arthritis, rheumatoid arthritis, polymyositis, dermatomyositis, osteoarthritis, dental pain, TMJ, spondylarthritis, ankylosing spondylitis, gout attacks, and pain management in cases of kidney stones and gallstones* An additional indication is the treatment of acute migraines. Diclofenac is used commonly to treat mild to moderate post-operative or post-traumatic pain, particularly when inflammation is also present, and is effective against menstrual pain and endometriosis.
5. A novel combined pharmaceutical composition as recited in Claim 1 wherein said another active ingredient is Glycofurol which is used as solvent to dissolve water- insoluble compounds. It is stable but combustible and incompatible with strong oxidizing agents. It is less painful, water soluble, less irritant, better bio availability, high effectiveness and ready to use. It has been reported to be non-toxic and non- irritating when diluted in water.
6. A novel combined pharmaceutical composition as recited in Claim 1 wherein said Drotaverine inhibits calmodulin (CM). The decrease in Ca2+ ions along with the inhibition of CM leads to the inhibition of "Calmodulin-Calcium Complex" (CM- Ca2+) formation. Drotaverine is well and quickly absorbed from jejunum and ileum. The peak plasma concentration reaches between 45-60 minutes. Half-life of absorption of Drotaverine is 12 minutes.
7. A novel combined pharmaceutical composition as recited in Claim 6 wherein said The onset of action of Drotaverine on oral administration is about 12 minutes and injectable form is very quick and it's safe in all kind of administration.
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| Application Number | Priority Date | Filing Date | Title |
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| IN1918/MUM/2011 | 2011-07-04 | ||
| IN1918MU2011 | 2011-07-04 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1183454A (en) | 1980-11-20 | 1985-03-05 | Beecham Group Limited | Pharmaceutical compositions |
| WO2000030715A1 (en) * | 1998-11-25 | 2000-06-02 | Chinoin Gyógyszer És Vegyészeti | Composition containing an analgesic and a xanthine or a xanthine derivative |
| WO2006079099A2 (en) | 2005-01-24 | 2006-07-27 | Amgen Inc. | Method of conjugating aminothiol containing molecules to a polymer |
| WO2006095363A2 (en) * | 2005-02-01 | 2006-09-14 | Troikaa Pharmaceuticals Ltd | Injectable preparations of diclofenic and its pharmaceutically acceptable salts |
| WO2007044693A2 (en) | 2005-10-07 | 2007-04-19 | The University Of Alabama | Multi-functional ionic liquid compositions |
-
2011
- 2011-12-19 WO PCT/IN2011/000868 patent/WO2013005226A1/en active Application Filing
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1183454A (en) | 1980-11-20 | 1985-03-05 | Beecham Group Limited | Pharmaceutical compositions |
| WO2000030715A1 (en) * | 1998-11-25 | 2000-06-02 | Chinoin Gyógyszer És Vegyészeti | Composition containing an analgesic and a xanthine or a xanthine derivative |
| WO2006079099A2 (en) | 2005-01-24 | 2006-07-27 | Amgen Inc. | Method of conjugating aminothiol containing molecules to a polymer |
| AU2006206166A1 (en) | 2005-01-24 | 2006-07-27 | Amgen Inc. | Method of conjugating aminothiol containing molecules a polymer |
| WO2006095363A2 (en) * | 2005-02-01 | 2006-09-14 | Troikaa Pharmaceuticals Ltd | Injectable preparations of diclofenic and its pharmaceutically acceptable salts |
| WO2007044693A2 (en) | 2005-10-07 | 2007-04-19 | The University Of Alabama | Multi-functional ionic liquid compositions |
| US20070093462A1 (en) | 2005-10-07 | 2007-04-26 | Rogers Robin D | Multi-functional ionic liquid compositions for overcoming polymorphism and imparting improved properties for active pharmaceutical, biological, nutritional, and energetic ingredients |
Non-Patent Citations (4)
| Title |
|---|
| ANONYMOUS: "Matched Brand/Brands of Diclofenac Potassium,Drotaverine", MEDGUIDEINDIA.COM, 2010, pages 1 - 1, XP055024035, Retrieved from the Internet <URL:http://www.medguideindia.com/find_brand_bygeneric.php?gen_mask=,115,388,> [retrieved on 20120405] * |
| BOLAJI O O ET AL: "Pharmacokinetics and bioavailability of drotaverine in humans", EUROPEAN JOURNAL OF DRUG METABOLISM AND PHARMACOKINETICS, EDITIONS MEDECINE ET HYGIENE, CHENE-BOURG, CH, vol. 21, no. 3, July 1996 (1996-07-01), pages 217 - 221, XP002665739, ISSN: 0378-7966 * |
| I. ROMICS ET AL: "The effect of drotaverine hydrochloride in acute colicky pain caused by renal and ureteric stones", BJU INTERNATIONAL, vol. 92, no. 1, 24 June 2003 (2003-06-24), pages 92 - 96, XP055024622, ISSN: 1464-4096, DOI: 10.1046/j.1464-410X.2003.04262.x * |
| MOTTU F ET AL: "ORGANIC SOLVENTS FOR PHARMACEUTICAL PARENTERALS AND EMBOLIC LIQUIDS: A REVIEW OF TOXICITY DATA", PDA JOURNAL OF PHARMACEUTICAL SCIENCE AND TECHNOLOGY, BETHESDA, MD, US, vol. 54, no. 6, 1 January 2000 (2000-01-01), pages 456 - 469, XP009066370, ISSN: 1079-7440 * |
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