EP1107738A4 - Nouvelle forme saline pharmaceutique - Google Patents

Nouvelle forme saline pharmaceutique

Info

Publication number
EP1107738A4
EP1107738A4 EP99968215A EP99968215A EP1107738A4 EP 1107738 A4 EP1107738 A4 EP 1107738A4 EP 99968215 A EP99968215 A EP 99968215A EP 99968215 A EP99968215 A EP 99968215A EP 1107738 A4 EP1107738 A4 EP 1107738A4
Authority
EP
European Patent Office
Prior art keywords
salt
agent
base
useful
saccharinate
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.)
Withdrawn
Application number
EP99968215A
Other languages
German (de)
English (en)
Other versions
EP1107738A1 (fr
Inventor
James W Rayburn
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.)
Bristol Myers Squibb Co
Original Assignee
Bristol Myers Squibb Co
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 Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co
Publication of EP1107738A1 publication Critical patent/EP1107738A1/fr
Publication of EP1107738A4 publication Critical patent/EP1107738A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • 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
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • A61P25/24—Antidepressants
    • 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]
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a novel salt form of certain pharmacologically active organic bases and their preparation.
  • the class will be exemplified by the saccharinate salt of buspirone, a useful anti-anxiety agent.
  • solubility of the salt is generally less than for more standard pharmaceutical salts such as halides, sulfates, and the like.
  • the saccharinate salt of certain non-al ⁇ kaloidal organic bases provides novel salt forms demonstrating improved organoleptic properties.
  • the saccharinate salt also provides a means of sustaining drug release by virtue of decreased aqueous solubility of the saccharinate compared to more standard pharmaceutical salts such as halides, sulfates, phosphates, and the like.
  • the saccharinate salts are conveniently synthesized by salt interchange on admixture of solutions of sodium saccharinate and acid addition salts; e.g., the hydrochloride salt, of medicinal organic bases.
  • Other salt-forming reactions well-known to one skilled in the pharmaceutical sciences, may also be employed.
  • antiinfectives such as erythromycin
  • analgesics such as codeine, meperidine, pentazocine, butorphanol, buprenorphine;
  • anxiolytics e.g., benzodiazepines such as alprazolam, azapirones such as buspirone;
  • antipsychotics e.g., phenothiazines such as chlorpramazine and thioridazine, piperazines such as fluphenazine, thioxanthenes such as thiothixene, butyrophenones such as haloperidol, dibenzoxapines such as loxapine, dihydroindolones such as molindone; and
  • affective disorder agents such as imipramine, trazodone, nefazodone, fluoxetine, sertraline, and the like, dextroamphetamine and methylphenidate.
  • Neurologies can be represented by procyclidine, biperiden, amantadine and selegiline; ergotamines and methylsergide; scopoiamine, cyclizine, hydroxyzine and the like.
  • Anesthetics are represented by benzocaine, dibucaine, lidocaine, procaine and the like.
  • Respiratory agents are represented by epinephrine, phenylephrine, phenylpropanolamine and pseudoephedrine; isoproterenol and terbutaline.
  • Cardiovasculars can be subclassed as:
  • inotropics such as dobutamine
  • antiarrhythmics such as acecainide, disopipramide;
  • ⁇ -blockers such as propranolol, atenolol, nadolol;
  • calcium blockers such as diltiazem, nifedipine and nimodipine;
  • vasodilators such as papaverine and isoxsuprine
  • antihypertensives such as hydralazine
  • diuretics such as triamterene and amiloride.
  • Endocrine agents such as bromocryptine and clomiphene; and metabolic agents such as phenformin.
  • Gastrointestinal agents such as metaclopramide or cimetidine.
  • the present invention involves stable crystalline saccharinate salts of orally administrable medicinal bases.
  • Saccharin chemically 1 ,2- benzisothiazol-3(2H)-one 1 ,1 , dioxide, is used as a sweetener, most commonly in the form of its sodium salt dihydrate. While it is used as a sweetener in pharmaceutical applications, its use is as a component of a mixture of ingredients.
  • saccharine provides a sweet taste in dilute aqueous solutions where it is about 500 times sweeter than sugar with the sweet taste still detectable in 1 :100,000 dilution; nonetheless saccharin has a bitter, metallic aftertaste. Because saccharin's taste is most pleasant in dilute solution, care must be exercised in formulating saccharin in its solid state because of a very objectionable taste.
  • the current invention relates to actual salt forms, as opposed to mixtures, comprising the organic base cation and the saccharinate anion.
  • the medicinal has pleasant organoleptic properties even in its solid form.
  • the saccharinate salts offer the potential for pharmaceutical formulations without requiring large amounts of other organoleptic enhancers such as sweeteners, flavors, and the like which are usually required to render medicinal bases palatable.
  • organoleptic enhancers such as sweeteners, flavors, and the like which are usually required to render medicinal bases palatable.
  • the advantages of saccharinate salts would especially be evident in formulating oral suspensions, chewable tablets, lozenges, and quick-melt dosage forms.
  • Another aspect of the present invention relates to the general reduction in solubility of the saccharinate salts of the non-alkaloidal medicinal bases compared to more common acid addition salts of the medicinal bases such as hydrohalide, sulfate, phosphate salts and the like.
  • the saccharinate salts offer a method for providing extended release dosing for certain medicinals.
  • Buspirone hydrochloride (8-4[4-(2-pyrimidinyl)-1 -piperazinyl])butyl]-8- azaspiro[4.5]decane-7,9-dione hydrochloride 4.22 g, 10 mmole) dissolved in a minimal amount of water was added to a concentrated solution of sodium saccharinate (2.05 g, 10 mmole) with stirring. The mixture was chilled and the supernatant aqueous layer decanted from the heavier oil layer which was dissolved in methylene chloride. The methylene chloride solution was washed with water and then dried (MgSO . The dried solution was filtered and concentrated in vacuo to a clear oil. Trituration in ether provided a pale yellow saccharinate salt, m.p. 142-145 °C.
  • Plate #1 contained buspirone hydrochloride.
  • Plate #2 contained buspirone saccharinate, and Plate #3 contained 1 :1 molar equivalent amounts of buspirone hydrochloride and sodium saccharinate in the form of a physical mixture.
  • Tasting volunteers were asked to taste each of the samples and give their preference. All volunteers selected Plate #2 (buspirone saccharinate) as the best tasting sample. By contrast, both Plates #1 and #3 were labeled as objectionable to highly objectionable in taste by the volunteers.

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Rheumatology (AREA)
  • Oncology (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Communicable Diseases (AREA)
  • Psychiatry (AREA)
  • Anesthesiology (AREA)
  • Urology & Nephrology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

L'invention concerne un sel de saccharinate de bases organiques médicinales qui ne sont pas des alcaloïdes, et constituant une nouvelle forme saline présentant des propriétés organoleptiques améliorées et une solubilité réduite.
EP99968215A 1998-08-27 1999-08-26 Nouvelle forme saline pharmaceutique Withdrawn EP1107738A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US9815498P 1998-08-27 1998-08-27
US98154P 1998-08-27
PCT/US1999/019575 WO2000012067A1 (fr) 1998-08-27 1999-08-26 Nouvelle forme saline pharmaceutique

Publications (2)

Publication Number Publication Date
EP1107738A1 EP1107738A1 (fr) 2001-06-20
EP1107738A4 true EP1107738A4 (fr) 2003-01-22

Family

ID=22267557

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99968215A Withdrawn EP1107738A4 (fr) 1998-08-27 1999-08-26 Nouvelle forme saline pharmaceutique

Country Status (6)

Country Link
EP (1) EP1107738A4 (fr)
JP (1) JP2003525855A (fr)
CN (1) CN1348363A (fr)
AU (1) AU6021199A (fr)
CA (1) CA2341522A1 (fr)
WO (1) WO2000012067A1 (fr)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19940740A1 (de) * 1999-08-31 2001-03-01 Gruenenthal Gmbh Pharmazeutische Salze
DE10013712A1 (de) * 2000-03-20 2001-09-27 Nutrinova Gmbh Nikotinsalze mit verbessertem Geschmack, Verfahren zu ihrer Herstellung und ihre Verwendung
DE10045521A1 (de) 2000-03-31 2001-10-04 Roche Diagnostics Gmbh Nukleinsäureamplifikationen
US20050176790A1 (en) 2001-02-28 2005-08-11 Johannes Bartholomaus Pharmaceutical salts
DE10109763A1 (de) * 2001-02-28 2002-09-05 Gruenenthal Gmbh Pharmazeutische Salze
DE10130504B4 (de) 2001-06-25 2005-02-03 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Xanthin- und Phenazon-Acesulfam-H-Komplexe mit verbessertem Geschmack, Verfahren zu ihrer Herstellung und ihre Verwendung
EP2275095A3 (fr) 2005-08-26 2011-08-17 Braincells, Inc. Neurogenese par modulation des recepteurs muscariniques
EP2258358A3 (fr) 2005-08-26 2011-09-07 Braincells, Inc. Neurogenèse avec un inhibiteur de l'acetylcholinestérase
EP1940389A2 (fr) 2005-10-21 2008-07-09 Braincells, Inc. Modulation de la neurogenese par inhibition de la pde
AU2006308889A1 (en) 2005-10-31 2007-05-10 Braincells, Inc. GABA receptor mediated modulation of neurogenesis
US20100216734A1 (en) 2006-03-08 2010-08-26 Braincells, Inc. Modulation of neurogenesis by nootropic agents
EP2382975A3 (fr) 2006-05-09 2012-02-29 Braincells, Inc. Neurogénèse par modulation d'angiotensine
US20100184806A1 (en) 2006-09-19 2010-07-22 Braincells, Inc. Modulation of neurogenesis by ppar agents
JP2011506374A (ja) * 2007-12-12 2011-03-03 ウルティモルフィクス・テクノロジーズ・ベー・フェー テノホビルジソプロキシルの固形物
US7935817B2 (en) 2008-03-31 2011-05-03 Apotex Pharmachem Inc. Salt form and cocrystals of adefovir dipivoxil and processes for preparation thereof
WO2010099217A1 (fr) 2009-02-25 2010-09-02 Braincells, Inc. Modulation de neurogenèse à l'aide de combinaisons de d-cyclosérine
DE202010001237U1 (de) 2010-01-21 2010-04-01 Grünenthal GmbH Kombination aus Tramadol und Acetaminophen als Brausetablette
EP2592078A1 (fr) 2011-11-11 2013-05-15 Almirall, S.A. Nouveaux dérivés de cyclohéxylamine dotés d'activités agonistes bêta 2 adrénergique et antagoniste muscarinique M3
TW201517906A (zh) * 2013-07-25 2015-05-16 Almirall Sa 含有ｍａｂａ化合物和皮質類固醇之組合
TW201617343A (zh) 2014-09-26 2016-05-16 阿爾米雷爾有限公司 具有β２腎上腺素促效劑及Ｍ３蕈毒拮抗劑活性之新穎雙環衍生物
CN107868117B (zh) * 2016-09-28 2021-04-23 中国科学院苏州纳米技术与纳米仿生研究所 司坦唑醇糖精盐及其制备方法和应用
NL2031332B1 (en) 2022-03-18 2023-09-29 Plethora Therapeutics B V Transmucosal delivery of psychoactive compounds

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1656M (fr) * 1960-12-19 1963-01-14 Tanabe Seiyaku Co Médicament a base de sels d'addition de l'acide benzophénone-2-carboxylique et de la 1-méthyl-3-(di-2-thiénylméthylene)-pipéridine.
EP0229000A2 (fr) * 1986-01-07 1987-07-15 Warner-Lambert Company Composition d'encapsulation pour gomme à mâcher et produits comestibles

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1288002A (fr) * 1954-06-14 1962-03-24 Pfizer & Co C Perfectionnements apportés aux procédés de fabrication de composés d'imidazoline
US5837277A (en) * 1992-06-04 1998-11-17 Smithkline Beecham Corporation Palatable pharmaceutical compositions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1656M (fr) * 1960-12-19 1963-01-14 Tanabe Seiyaku Co Médicament a base de sels d'addition de l'acide benzophénone-2-carboxylique et de la 1-méthyl-3-(di-2-thiénylméthylene)-pipéridine.
EP0229000A2 (fr) * 1986-01-07 1987-07-15 Warner-Lambert Company Composition d'encapsulation pour gomme à mâcher et produits comestibles

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002221043, Database accession no. 1963:461311 *
See also references of WO0012067A1 *

Also Published As

Publication number Publication date
EP1107738A1 (fr) 2001-06-20
JP2003525855A (ja) 2003-09-02
WO2000012067A1 (fr) 2000-03-09
AU6021199A (en) 2000-03-21
CA2341522A1 (fr) 2000-03-09
CN1348363A (zh) 2002-05-08

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