[go: up one dir, main page]

CN101484132A - Pleasant-tasting ranitidine formulation - Google Patents

Pleasant-tasting ranitidine formulation Download PDF

Info

Publication number
CN101484132A
CN101484132A CNA2007800003510A CN200780000351A CN101484132A CN 101484132 A CN101484132 A CN 101484132A CN A2007800003510 A CNA2007800003510 A CN A2007800003510A CN 200780000351 A CN200780000351 A CN 200780000351A CN 101484132 A CN101484132 A CN 101484132A
Authority
CN
China
Prior art keywords
preparation
ranitidine
citrate
methyl
nitroethylene
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.)
Pending
Application number
CNA2007800003510A
Other languages
Chinese (zh)
Inventor
R·刘易斯
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cypress Pharmaceuticals Inc
Original Assignee
Cypress Pharmaceuticals Inc
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.)
Filing date
Publication date
Application filed by Cypress Pharmaceuticals Inc filed Critical Cypress Pharmaceuticals Inc
Publication of CN101484132A publication Critical patent/CN101484132A/en
Pending legal-status Critical Current

Links

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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels

Landscapes

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

Abstract

Disclosed is a pleasant-tasting formulation of an H2-antagonist for oral administration to a human subject.

Description

Ranitidine formulation with desirable taste
Priority of the present invention
The application requires the U.S. Provisional Patent Application US60/948 of submission on July 9th, 2007, and 606 priority is incorporated herein by reference this application.
Background of invention
Gastroesophageal reflux is child's a main pathogenic factor [Sandhu and Sawzcenko, IndianJ Pediatr 66 (Suppl 1), S5].In fact, gastroesophageal reflux disease (GERD) has higher incidence [Cezard the baby rather than in big slightly child of age or adult, Digestion 66 (Suppl 1), 3], [Vandenplas etc. frequently take place during the earlier month of life usually, Early Hum Dev 81,1011].Take place at night, disturb the GERD of sleep pattern to need special concern [Orr, Eur J Gastroenterol Hepatol 17,113].
In the verified medicine that can be used for treating GERD histamine H2 receptor antagonist is arranged, comprise cimetidine, famotidine, nizatidine and ranitidine [Tougas and Armstrong, Can JGastroenterol 11 (Suppl B), 51B].These medicines have bitterness separately, and known baby refuses the liquid [Kajiura etc., Dev Psychobiol, 25,375] of bitterness.Yet, in order to adhere to therapeutic scheme to greatest extent, trend towards the preferred oral liquid dosage form for baby and big slightly children taking of age, even also be so [Schaefer and Michaelis to extremely bitter activating agent, J Antimicrob Chemother 34 (Suppl A), 33].
The H2-antagonist is easily degraded.Catabolite comprises: 1-[2-(5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene, be called " related compound C "; (N-[2-(5-[(dimethylamino methyl)-2-furan sulfenyl] ethyl)-N '-methyl-2-nitroethylene-1,1-diamidogen N-oxide], be called " related compound X ".The useful oral liquid of H2-antagonist is stable and the limited preparation of degrading.
The oral liquid of the H2-antagonist of several prior aries all comprises ethanol.Owing to multiple reason, comprise to the worry that whether conforms with drug specifications and directly pharmacotoxicological effect and ethanol issuable toxicity in the child, so need have the oral liquid that is substantially free of alcoholic acid H2-antagonist.
Therefore, need have and have desirable taste and stable and oral liquid that do not contain alcoholic acid H2-antagonist.The invention provides such preparation.
Summary of the invention
The present invention has several aspects, particularly including following aspect:
Aspect 1. does not contain the alcoholic acid ranitidine hydrochloride aqueous solution preparation that is suitable for people curee's oral administration, said preparation comprises ranitidine and pharmaceutically acceptable citrate and other optional pharmaceutically acceptable excipient, and wherein in the suitable closed container system under being stored in 40 degrees centigrade and 75% relative humidity in about 1 month formulation samples, the ratio that is present in ranitidine and the ranitidine of labeled marker in this sample is not less than about 90%.
The preparation of 2. aspects 1, aspect, wherein in the suitable closed container system under being stored in 40 degrees centigrade and 75% relative humidity in about 2 months formulation samples, the ranitidine that exists in this sample is not less than about 90% with the ratio of the ranitidine of labeled marker.
The preparation of 3. aspects 2, aspect, wherein in the suitable closed container system under being stored in 40 degrees centigrade and 75% relative humidity in about 3 months formulation samples, the ranitidine that exists in this sample is not less than about 90% with the ratio of the ranitidine of labeled marker.
4. aspects 1,2, aspect or 3 preparation comprise the citrate of about 0.1%-about 3% (wt./vol.).
The preparation of 5. aspects 4, aspect comprises the citrate of about 0.5%-about 2%.
The preparation of 6. aspects 5, aspect comprises about 1% citrate.
The preparation of 7. aspects 6, aspect comprises about 1% Trisodium citrate dihydrate.
The preparation of any among the aspect 8. aspect 4-7, wherein the pH of said preparation is about 7.1-about 7.3.
The preparation of any further comprises the Fructus Vitis viniferae correctives among the aspect 9. aspect 4-8.
The preparation of any in the 10. above-mentioned aspects, aspect, wherein method A is used to measure the ratio of the ranitidine that is present in this sample and the ranitidine of labeled marker.
Aspect 11. does not contain the alcoholic acid ranitidine hydrochloride aqueous solution preparation that is suitable for people curee's oral administration; said preparation comprises ranitidine and pharmaceutically acceptable citrate and other optional pharmaceutically acceptable excipient; and wherein in the suitable closed container system under being stored in 40 degrees centigrade and 75% relative humidity in about 1 month formulation samples, the 1-[2-in this sample (5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene and 1-[2-(5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene adds that the ratio of the summation of ranitidine is no more than about 1%.
The preparation of 12. aspects 11, aspect; wherein in the suitable closed container system under being stored in 40 degrees centigrade and 75% relative humidity in about 2 months formulation samples, the 1-[2-in this sample (5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene and 1-[2-(5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene adds that the ratio of the summation of ranitidine is no more than about 1%.
The preparation of 13. aspects 12, aspect; wherein in the suitable closed container system under being stored in 40 degrees centigrade and 75% relative humidity in about 3 months formulation samples, the 1-[2-in this sample (5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene and 1-[2-(5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene adds that the ratio of the summation of ranitidine is no more than about 1%.
14. aspects 11,12, aspect or 13 preparation comprise the citrate of about 0.1%-about 3% (wt./vol.).
The preparation of 15. aspects 14, aspect comprises the citrate of about 0.5%-about 2%.
The preparation of 16. aspects 15, aspect comprises about 1% citrate.
The preparation of 17. aspects 16, aspect comprises about 1% Trisodium citrate dihydrate.
The preparation of any among the aspect 18. aspect 14-17, wherein the pH of said preparation is about 7.1-about 7.3.
The preparation of any further comprises the Fructus Vitis viniferae correctives among the aspect 19. aspect 14-18.
The preparation of any in the 20. above-mentioned aspects, aspect, wherein method A is used to measure 1-[2-(5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene and 1-[2-(5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene adds the ratio of the summation of ranitidine.
Describe in detail and embodiment
Used term " does not contain ethanol " and " no ethanol " and " shortage ethanol " is equal to each other among the present invention.They represent not exist the ethanol of substantive concentration separately, but do not get rid of idol ethanol are not arranged, such as being present in the excipient as impurity.For example, alcoholic acid final concentration is not " not containing ethanol " greater than about 1% preparation.
Research and develop and tested the alcoholic acid several formulations of shortage.Estimated the taste of preparation.It is relevant with good to eat taste that discovery comprises a certain amount of saccharin sodium, sodium chloride and sorbitol.It is relevant with agreeable to the taste especially taste further to comprise a certain amount of Fructus Vitis viniferae correctives, but, can use the combination of any correctives and sweetener.Also estimated stability of formulation.Comprising a certain amount of citrate in preparation is correlated with favourable stability relevant (formation of related compound C is slowed down) and with agreeable to the taste taste.Preparation of the present invention can comprise any pharmaceutically acceptable salt of citric acid, and special optimization citric acid sodium dihydrate.Preparation of the present invention can comprise about 3% (wt./vol.) of about 0.1%-, and preferably about 0.5%-is about 2%, and preferred about 1% Trisodium citrate dihydrate especially.Appropriate formulation can also comprise other stabilizing agent (for example parabens), thickening agent, buffer agent etc.In a preferred embodiment, thickening agent comprises hypromellose, and this preparation is substantially free of for example cellulose gum (sodium carboxymethyl cellulose).In another preferred embodiment, thickening agent comprises cellulose gum (sodium carboxymethyl cellulose), and is substantially free of hypromellose.The example of the type of preparation of research and development and test is as shown in following table 1:
Figure A200780000351D00091
The method that shows stability of empirical tests can be used to measure ranitidine hydrochloride, related compound C and related compound X.Use specific this method and in this application it is called " method A ".Typical set and condition as the method A that carries out in appropriate H PLC system are described below.The standard substance of ranitidine and related compound C can be available from USP.Needs dilution standard product and sample according to optimum detection.Set the UV detector so that detect at the 322nm place.Used chromatographic column is Zorbax SB CN, 150nm X 4.6mm, Ca t# 863953.905 or equivalent post.Column temperature is an ambient temperature.Volume injected is generally 10 microlitres.Mobile phase A is made by mixing 950mL 0.1M ammonium acetate, 50mL acetonitrile, 10mL acetic acid and 2mL triethylamine.Mobile phase B is made by mixing 700mL 0.1M ammonium acetate, 300mL acetonitrile, 10mL acetic acid and 2mL triethylamine.The typical stream dynamic program is as shown in following table 2.
Table 2
Time ％A ％B Flow velocity [ml/ minute]
0 100 0 0.5
5.5 minute 100 0 0.5
5.6 minute 100 0 1.7
18.0 minute 100 0 1.7
18.1 minute 0 100 1.0
34.0 minute 0 100 1.0
34.1 minute 100 - 1.7
40.0 minute 100 - 1.7
Annotate: can appropriateness adjust flow velocity and temporal sequence so that the peak eluting on the Chromatogram Baseline acromion that obtains the required retention time at specific peak and/or guarantee not have to be paid close attention to, described Chromatogram Baseline acromion occurs because of the mobile phase flow program becomes B or becomes A from B from A.
The further detailed content of method A is as implementing in pharmaceutical field usually.Observe different peaks for ranitidine.To generally observed another the different peak of related compound C, and related compound X is observed another peak.If any, so when analytic sample observed all other peaks all be considered to be " other related substances ".Calculate and write down the area response value at each peak.Calculate the %:P of single material according to following equation i=(Rs iX100)/(Ru x CC i), Rs wherein iThe area response value of single material in the=sample; The area response value sum of ranitidine, related compound C, related compound X and any unknown materials in the Ru=sample; CC i=response factor that single material is compared with ranitidine.With regard to the material of any the unknown, CC iGet 1.Total impurities percentage ratio is each P of the material of non-ranitidine iSummation.According to reasonably estimating in the pharmaceutical field, generally as follows at retention time (RT), relative retention time (RRT) and the response factor (CC) at 322nm place, but can change to a certain extent: related compound C:RT=6.1; RRT=0.6; CC=0.97; Related compound X:RT=13.1; RRT=1.3; CC=0.77; Ranitidine: RT=10.1; RRT=1; CC=1.
Can be prepared as follows preparation of the present invention.The water of first's volume is put into first container and is heated to 75-80 degree centigrade.Then can be with water-fast relatively any material at room temperature, sneak into such as parabens in the water of first's volume and form first kind of solution until dissolving.At room temperature the water of second portion volume is put into second container.To at room temperature water-soluble relatively any material then sneaks in the water of second portion volume until second kind of solution of dissolving formation.First kind of solution is cooled to room temperature.In case first kind of solution is cooled to room temperature, first kind and second kind of solution is mixed mutually forming mutual blended solution immediately.Measure the pH of this mutual mixed solution and if necessary, pH is adjusted to required pH, about 7.3 such as being adjusted to about 7.1-, so that form the mutual mixed solution that pH adjusts.In the mutual mixed solution that pH adjusts, add pure water USP (in right amount),, thereby form preparation of the present invention so that obtain required final solution volume.
Can for example alleviating to needs, the human patients of one or more GERD symptoms gives preparation of the present invention.For example, can be by oral, for example, give the preparation of the present invention of certain volume, so that for example about 5mg/kg/ days of acquisition-Yue 10mg/kg/ days dosage with spoon or with medicine dropper B.I.D..
When the preparation in the preparation table 1, be made into the preparation of the ranitidine hydrochloride that comprises 1.68% (wt./vol.).Owing to this reason, so the ranitidine hydrochloride of 1.68% (wt./vol.) can be called " labeled marker ".
As another embodiment, estimated the stability of formulation that comprises sodium citrate in the table 1.Generally be placed in the suitable closed container system under the controlled environment of uniform temperature and relative humidity one period regular time and carry out this class estimation of stability by preparation with certain volume.This class results of stability comprises those contents shown in the following table 3, wherein each " standard " refers to the specification requirement of estimating that each preparation should satisfy, and each " experiment " refers to the instantiation of the preparation that satisfies one or more standards:
Table 3
Time Temperature RH The ranitidine % of labeled marker Related compound C
Standard A 1 month 40C. 75％ NLT?90％ NMT?1％
Experiment B 2 months 40C. 75％ 97.8％ 0.64％
Experiment C 2 months 40C. 75％ 97.1％ 0.55％
Standard D 2 months 40C. 75％ NLT?90％ NMT?1％
Experiment E 3 months 40C. 75％ 95.6％ 0.87％
Experiment F 3 months 40C. 75％ 96.0％ 0.72％
Standard G 3 months 40C. 75％ NLT?90％ NMT?1％
Experiment H 3 months 25C. 60％ 98.8％ 0.26％
Experiment I 3 months 25C. 60％ 99.0％ 0.21％
Standard J 3 months 25C. 60％ NLT?90％ NMT?1％
(" NLT " expression " is not less than "; " NMT " expression " is no more than ")
All publications, patent and patent application are incorporated herein by reference.Disclosed in this manual content so far has been not the qualification effect as embodiment only.The equivalence techniques scheme will be apparent to those skilled in the art.Therefore, the present invention will only limit to and the suitable consistent legal and reasonable range of following claim, comprise any He all equivalence techniques schemes.

Claims (20)

1. do not contain the alcoholic acid ranitidine hydrochloride aqueous solution preparation that is suitable for people curee's oral administration, said preparation comprises ranitidine and pharmaceutically acceptable citrate and other optional pharmaceutically acceptable excipient, and wherein in the suitable closed container system under being stored in 40 degrees centigrade and 75% relative humidity in about 1 month formulation samples, the ratio that is present in ranitidine and the ranitidine of labeled marker in the sample is not less than about 90%.
2. the preparation of claim 1, wherein in the suitable closed container system under being stored in 40 degrees centigrade and 75% relative humidity in about 2 months formulation samples, the ranitidine that exists in this sample is not less than about 90% with the ratio of the ranitidine of labeled marker.
3. the preparation of claim 2, wherein in the suitable closed container system under being stored in 40 degrees centigrade and 75% relative humidity in about 3 months formulation samples, the ranitidine that exists in this sample is not less than about 90% with the ratio of the ranitidine of labeled marker.
4. the preparation of claim 1 comprises the citrate of about 0.1%-about 3% (wt./vol.).
5. the preparation of claim 4 comprises the citrate of about 0.5%-about 2%.
6. the preparation of claim 5 comprises about 1% citrate.
7. the preparation of claim 6 comprises about 1% Trisodium citrate dihydrate.
8. each preparation among the claim 4-7, wherein the pH of said preparation is about 7.1-about 7.3.
9. each preparation among the claim 1-7 further comprises the Fructus Vitis viniferae correctives.
10. each preparation among the claim 1-7, wherein method A is used to measure the ratio of the ranitidine that is present in this sample and the ranitidine of labeled marker.
11. do not contain the alcoholic acid ranitidine hydrochloride aqueous solution preparation that is suitable for people curee's oral administration; said preparation comprises ranitidine and pharmaceutically acceptable citrate and other optional pharmaceutically acceptable excipient; and wherein in the suitable closed container system under being stored in 40 degrees centigrade and 75% relative humidity in about 1 month formulation samples, the 1-[2-in this sample (5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene and 1-[2-(5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene add ranitidine and ratio be no more than about 1%.
12. the preparation of claim 11; wherein in the suitable closed container system under being stored in 40 degrees centigrade and 75% relative humidity in about 2 months formulation samples, the 1-[2-in this sample (5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene and 1-[2-(5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene add ranitidine and ratio be no more than about 1%.
13. the preparation of claim 12; wherein in the suitable closed container system under being stored in 40 degrees centigrade and 75% relative humidity in about 3 months formulation samples, the 1-[2-in this sample (5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene and 1-[2-(5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene add ranitidine and ratio be no more than about 1%.
14. the preparation of claim 11 comprises the citrate of about 0.1%-about 3% (wt./vol.).
15. the preparation of claim 14 comprises the citrate of about 0.5%-about 2%.
16. the preparation of claim 15 comprises about 1% citrate.
17. the preparation of claim 16 comprises about 1% Trisodium citrate dihydrate.
18. each preparation among the claim 14-17, wherein the pH of said preparation is about 7.1-about 7.3.
19. each preparation among the claim 11-17 further comprises the Fructus Vitis viniferae correctives.
20. each preparation among the claim 11-17, wherein method A is used to measure 1-[2-(5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene and 1-[2-(5-dimethylamino methyl)-2-furyl] methyl sulfinyl] ethylamino]-1-aminomethyl-2-nitroethylene add ranitidine and ratio.
CNA2007800003510A 2007-07-09 2007-08-29 Pleasant-tasting ranitidine formulation Pending CN101484132A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US94860607P 2007-07-09 2007-07-09
US60/948,606 2007-07-09

Publications (1)

Publication Number Publication Date
CN101484132A true CN101484132A (en) 2009-07-15

Family

ID=39485145

Family Applications (1)

Application Number Title Priority Date Filing Date
CNA2007800003510A Pending CN101484132A (en) 2007-07-09 2007-08-29 Pleasant-tasting ranitidine formulation

Country Status (3)

Country Link
CN (1) CN101484132A (en)
AU (2) AU2007216671B2 (en)
WO (1) WO2009008895A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102010019575A1 (en) 2010-05-05 2012-01-19 Rainer Pommersheim Solar collector for use in building for heating air and/or water by solar power, has absorber, where flow direction and flow angle of heat carrier medium flow is preset by absorber and aligned in collector surface in position of modules
ES2684594B1 (en) * 2017-03-29 2019-05-16 Farmalider Sa Aqueous solution of ranitidine free of ethanol
ES2722673B2 (en) * 2018-02-12 2021-03-29 Farmalider Sa Aqueous ranitidine solution

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2633181B1 (en) * 1988-06-24 1992-01-10 Glaxo Lab Sa RANITIDINE-BASED PHARMACEUTICAL COMPOSITION AND PROCESS FOR PREPARING THE SAME
CH679582A5 (en) * 1988-07-18 1992-03-13 Glaxo Group Ltd
GB9004328D0 (en) * 1990-02-27 1990-04-25 Glaxo Group Ltd Chemical compounds
WO1995010274A1 (en) * 1993-10-14 1995-04-20 F.H. Faulding & Co. Limited Aqueous pharmaceutical composition
GB9418530D0 (en) * 1994-09-14 1994-11-02 Glaxo Group Ltd Medicaments
US5728401A (en) * 1997-04-16 1998-03-17 Ranbaxy Laboratories, Ltd. Effervescent ranitidine formulations

Also Published As

Publication number Publication date
AU2007216671B2 (en) 2009-07-16
AU2007216671A1 (en) 2009-01-29
AU2009202308A1 (en) 2009-07-02
WO2009008895A1 (en) 2009-01-15

Similar Documents

Publication Publication Date Title
US12171768B2 (en) IRAK4 degraders and uses thereof
Leijen et al. A phase I, open-label, randomized crossover study to assess the effect of dosing of the MEK 1/2 inhibitor Selumetinib (AZD6244; ARRY-142866) in the presence and absence of food in patients with advanced solid tumors
TW200829571A (en) Liquid preparation comprising pimobendan
JP5255429B2 (en) Pharmaceutical composition containing oseltamivir phosphate
Santoveña et al. Design of a pediatric oral formulation with a low proportion of hydrochlorothiazide
US20220323429A1 (en) Pimavanserin for treating neurodegenerative diseases
Wollmer et al. A biopredictive in vitro approach for assessing compatibility of a novel pediatric hydrocortisone drug product within common pediatric dosing vehicles
CN101484132A (en) Pleasant-tasting ranitidine formulation
Tuesuwan et al. Basis to aid crisis: Favipiravir oral solution for hospital compounding during COVID-19 drug shortage
CN104173286A (en) Azelastine composition and use
CN103054813A (en) Azithromycin oral sustained-release dry suspension and preparation method thereof
De Goede et al. Development and validation of a paediatric oral formulation of clonidine hydrochloride
KR20090086686A (en) Silymarin-containing pharmaceutical composition with improved dissolution rate and preparation method thereof
KR102219919B1 (en) Composition comprising hydrocortisone
CN104306331B (en) A kind of Cetirizine Hydrochloride syrup
Cho et al. Development of a novel combination tablet containing trimebutine maleate and mosapride citrate for the treatment of functional dyspepsia
Klovrzová et al. Pediatric oral solutions with propranolol hydrochloride for extemporaneous compounding: the formulation and stability study
Kulkarni et al. Design, development and scale up studies of metformin hydrochloride multiparticulate system: A promising alternative to large size tablet
WO2022222886A1 (en) Elagolix sodium composition
WO2017037232A1 (en) Anidulafungin formulations
Brown et al. Effect of oral contraceptives on the transport of chlorpromazine across the CACO-2 intestinal epithelial cell line
CN1891212B (en) Oral preparation and its preparing method
Malhotra et al. The pharmacokinetic profile of fesoterodine 8 mg with daytime or nighttime dosing
US20170319480A1 (en) Pharmaceutical formulation
CN111450050A (en) Loperamide hydrochloride oral solution and preparation method thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C02 Deemed withdrawal of patent application after publication (patent law 2001)
WD01 Invention patent application deemed withdrawn after publication

Open date: 20090715