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WO1994014490A1 - Bloc de medicament sous forme compactee pour la production de particules inhalables de substance active - Google Patents

Bloc de medicament sous forme compactee pour la production de particules inhalables de substance active Download PDF

Info

Publication number
WO1994014490A1
WO1994014490A1 PCT/EP1993/001158 EP9301158W WO9414490A1 WO 1994014490 A1 WO1994014490 A1 WO 1994014490A1 EP 9301158 W EP9301158 W EP 9301158W WO 9414490 A1 WO9414490 A1 WO 9414490A1
Authority
WO
WIPO (PCT)
Prior art keywords
drug
solidified
group
solid structure
pharmaceutical
Prior art date
Application number
PCT/EP1993/001158
Other languages
German (de)
English (en)
Inventor
Bernhard Hugemann
Hans G. Burgschat
Helmut Heide
Joachim Pabst
Original Assignee
Bernhard Hugemann
Burgschat Hans G
Helmut Heide
Joachim Pabst
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 Bernhard Hugemann, Burgschat Hans G, Helmut Heide, Joachim Pabst filed Critical Bernhard Hugemann
Priority to AU40666/93A priority Critical patent/AU4066693A/en
Publication of WO1994014490A1 publication Critical patent/WO1994014490A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M15/00—Inhalators
    • A61M15/0065—Inhalators with dosage or measuring devices
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M2202/00—Special media to be introduced, removed or treated
    • A61M2202/06—Solids
    • A61M2202/062—Desiccants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M2202/00—Special media to be introduced, removed or treated
    • A61M2202/06—Solids
    • A61M2202/064—Powder
    • A61M2202/066—Powder made from a compacted product by abrading

Definitions

  • the invention relates to a solidified drug supply in the form of a solid, from which mechanical tools, such as e.g. a milling machine, active ingredient particles are processed and sucked into the respiratory tract by inhalation.
  • mechanical tools such as e.g. a milling machine
  • Micronized powders tend to agglomerate almost immediately and then form larger particle composites which are no longer inhalable or which cannot be left in a reproducible manner at all from the metering devices.
  • CORRECTED SHEET (RULE 91) segregate during transport. This relates in particular to powder mixtures of different substances. Due to the very large specific surface area, micronized powders are chemically very active and tend to be unstable in storage (water absorption, oxidation and the like).
  • inhaler systems which are based on the use of loose or slightly compacted micronized starting materials are unsatisfactory in their function with regard to metering accuracy, drug safety, method of operation and long-term stability.
  • the object of the invention is a solidified drug supply for the mechanical production of inhalable active ingredient particles, which avoids the disadvantages mentioned.
  • the drug supply have an isotropic solid structure. This means that in a monolithic solid, the bond strength from grain to grain is in the same order of magnitude as the specific inherent strength of the constituent components. The strength, density and composition of the solid are homogeneous.
  • the solid and homogeneous structure of the drug supply according to the invention allows a defined and thus a Processing of quantities of active substance particles reproducible in the dosage. Loosely integrated particle composites and agglomerates cannot arise.
  • the solidified drug supply can be produced in any form. This is preferably designed as a thick-walled ring body. This geometrical design of the drug supply has the following advantages:
  • the inner cavity of the ring can be used as the beginning of the inhalation tube, so that the active substance particles can enter the inhalation tube immediately after their generation. This avoids dead flow zones.
  • the wall thickness can be selected such that the differences in the speeds of the processing element on the inner and outer ring diameters with respect to the total area are negligible. As is well known, the speed in the center of a full body would be zero. This would lead to an undefined removal of the active substance body and thus undefined particle generation.
  • the medicinal substance supply according to the invention can be produced from pure medicinal substances alone or medicinal substance-carrier substance combinations which can be inhaled as aerosols and used for the treatment of certain diseases.
  • the pharmaceutical preparation according to the invention not only eliminates the established pharmaceuticals but also others, so far not via the Respiratory active ingredients that can be inhaled. These are in particular:
  • Respiratory therapy e.g. from the group of betamimetics: fenoterol,
  • Insulin, calcitonin, desmopressin and others Drugs to combat addiction nicotine, methadone, levo ethadone and others Narcoanalgetica / neuroleptanalgetica buprenorphine, dehydrocodeine, fentanyl and others Alkaloids e.g. Scopol amine and others
  • Chemotherapy drugs e.g. Pentamidine and others
  • These active substances can be mixed in powder form, alone or in a homogeneous distribution, with neutral additives which are suitable for inhalation application.
  • the following functions can be predetermined by using these additives - Dilution of highly effective drugs
  • the currently neutral effect carriers are e.g. Lactose, glucose, mannitol, table salt and mixtures of these come into question, which have proven to be advantageous for setting certain processing and abrasion properties and for diluting the active ingredients in the abrasion particles.
  • solidified drug stocks with an isotropic solid structure are made from pourable pharmaceutical preparations, preferably granules, by isostatic pressing at pressures between 50 and 500 megapascals.
  • Isostatic pressing means the uniform pressure transfer to the bulk material on all sides.
  • appropriately shaped elastic matrices are used, for example, which are deformed to the desired body by means of hydraulic pressure. This creates a homogeneous, uniformly dense and textureless structure that optimally fulfills the requirements for medicinal substance stocks in inhalers.
  • injection molding of plasticized materials, melting processes, die casting and the like is used for the production of isotropically solidified drug stocks.
  • the resistance of the preparation form according to the invention to chemical aging, moisture absorption and other changes (storage stability) is another beneficial property.
  • reducing the active surface area as a result of the compacting of the starting materials according to the invention a considerable improvement in the storage stability is achieved.
  • FIG. 1 shows in section the packaging unit of the medicament supply according to the invention
  • Fig. 3 shows a corresponding measurement curve of the generated microparticles from a ring tablet made according to the invention from this powder (Fig.2).
  • the necessary storage stability is supported by appropriate packaging of the drug supply 2 (FIG. 1).
  • the drug supply 2 according to the invention is inserted into an inhalation tube 1 and is exchanged together with the inhalation tube when the used active substance body is replaced.
  • the drug stock and the inhalation tube are housed together in a container that also serves as a cap for the inhaler.
  • the closure cap 5 in which there is a desiccant which reliably protects the medicament supply in the form of the ring tablet 2 from moisture absorption. Since the closure cap 5 when the inhalation tube 1 and the medicament are replaced If, at the same time, advice serves as the sealing cap of an aerosol generator, the drying agent 6 remains with the drug supply over the entire consumption period and is only replaced after it has been used by a new unit consisting of inhalation tube 1, drug supply 2, sealing cap 5 and drying agent 6. 1, a base element 3, into which the inhalation tube 1 is snapped in by means of a “snap-in device” 4, is completed in a manner safe from mechanical and chemical destruction in the packaging unit according to the invention. A hermetic seal of the entire packaging is provided by a second one
  • FIGS. 2 and 3 are original plotter diagrams of the particle size distribution according to the volume fractions, namely in FIG. 2 of the non-micronized starting mixture of 25% salbutamol and 75% lactose. 3 shows the particle size distribution of the mechanically generated aerosol from a ring tablet made according to the invention from this mixture, which was homogeneously compressed by isostatic pressing at 250 MPa according to a particularly advantageous method of manufacture.
  • the particle distribution of the starting mixture extends over a very large range between 0 and over 200 ⁇ * n particle or granule diameter. In the actual respiratory range between 0.5 to approx. 10A **, this represented only very small proportions.
  • Fig. 3 the particle distribution after mechanical aerosol generation from a ring tablet is shown, which was prepared from the above-mentioned starting mixture. As can be seen, there are only inhalable, respirable particles in the range from 0.5 to 7.5 t ⁇ m in this spectrum, with total amounts - depending on the drug - being adjustable between approximately 10 to 5000 micrograms.

Landscapes

  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pulmonology (AREA)
  • Anesthesiology (AREA)
  • Biomedical Technology (AREA)
  • Biophysics (AREA)
  • Hematology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Preparation (AREA)
  • Medical Preparation Storing Or Oral Administration Devices (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne un bloc de médicament sous forme compactée comportant une structure de solide isotrope, qui est produite par compression isostatique.
PCT/EP1993/001158 1992-12-23 1993-05-11 Bloc de medicament sous forme compactee pour la production de particules inhalables de substance active WO1994014490A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU40666/93A AU4066693A (en) 1992-12-23 1993-05-11 Compacted drug body for use in the mechanical generation of inhalable active-substance particles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4243649.4 1992-12-23
DE4243649 1992-12-23

Publications (1)

Publication Number Publication Date
WO1994014490A1 true WO1994014490A1 (fr) 1994-07-07

Family

ID=6476237

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/001158 WO1994014490A1 (fr) 1992-12-23 1993-05-11 Bloc de medicament sous forme compactee pour la production de particules inhalables de substance active

Country Status (3)

Country Link
JP (1) JPH06339513A (fr)
AU (1) AU4066693A (fr)
WO (1) WO1994014490A1 (fr)

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4429707C1 (de) * 1994-08-04 1996-02-01 Bernhard Dipl Ing Hugemann Inhalator mit integrierter, verfestigter, ringförmiger Wirkstofftablette
WO1999029432A1 (fr) * 1997-12-05 1999-06-17 Palas Gmbh Procede et dispositif pour la production d'un aerosol solide
WO1999061003A1 (fr) * 1998-05-27 1999-12-02 Euroceltique S.A. Systeme de presentation de medicament comprenant de la matiere medicamenteuse solide fortement compactee
WO2001085174A1 (fr) * 2000-05-12 2001-11-15 Chiesi Farmaceutici S.P.A. Formulations contenant un medicament a base de glucocorticoides destinees au traitement des maladies broncho-pulmonaires
US6964759B2 (en) 2000-02-22 2005-11-15 Chiesi Farmaceutici S.P.A. Formulations containing an anticholinergic drug for the treatment of chronic obstructive pulmonary disease
US6967017B1 (en) 1999-07-23 2005-11-22 Chiesi Farmaceutici S.P.A. Formulations of steroid solutions for inhalatory administration
US7018618B2 (en) 2000-05-22 2006-03-28 Chiesi Farmaceutici S.P.A. Stable pharmaceutical solution formulations for pressurized metered dose inhalers
DE102005028696A1 (de) * 2005-06-21 2006-12-28 Pulmotec Gmbh Verwendung eines Hilfsstoffs zur Einstellung der Abrasionsfestigkeit eines verfestigten Wirkstoffpräparats
US7220737B1 (en) 1997-09-04 2007-05-22 Novoneuron, Inc Noribogaine in the treatment of pain and drug addiction
US7223381B2 (en) 1998-11-25 2007-05-29 Chiesi Farmaceutici S.P.A. Pressurised metered dose inhalers (MDI)
US7297344B1 (en) 1999-05-27 2007-11-20 Euro-Celtique, S.A. Preparations for the promotion of wound healing in the upper respiratory tract and/or ear
US7300667B1 (en) 1999-05-27 2007-11-27 Euro-Celtique, S.A. Preparations for the application of anti-inflammatory, especially antiseptic agents and/or agents promoting the healing of wounds, to the lower respiratory tract
US7381402B2 (en) 2004-02-27 2008-06-03 Chiesi Farmaceutici S.P.A. Stable pharmaceutical solution formulations for pressurized metered dose inhalers
EP1941868A2 (fr) 2000-02-28 2008-07-09 PharmaKodex Limited Améliorations portant sur ou en relation avec l'administration orale de médicaments
US7468194B1 (en) 1999-05-27 2008-12-23 Euro-Celtique, S.A. Preparations for the application of anti-inflammatory agents
US7601336B2 (en) 1997-06-13 2009-10-13 Chiesi Farmaceutici S.P.A. Pharmaceutical aerosol composition
US7696178B2 (en) 2001-07-02 2010-04-13 Chiesi Farmaceutici S.P.A. Optimised formulation of tobramycin for aerosolization
US7754710B2 (en) 1997-09-04 2010-07-13 Novoneuron, Inc. Noribogaine in the treatment of pain and drug addiction
US8362007B1 (en) 2010-05-11 2013-01-29 Demerx, Inc. Substituted noribogaine
US8381721B2 (en) 2008-09-26 2013-02-26 Oriel Therapeutics, Inc. Dry powder inhalers with dual piercing members and related devices and methods
US8550071B2 (en) 2008-09-26 2013-10-08 Oriel Therapeutics, Inc. Inhalers with airway disks having discrete airway channels and related disks and methods
US8637648B1 (en) 2010-06-22 2014-01-28 Demerx, Inc. Compositions comprising noribogaine and an excipient to facilitate transport across the blood brain barrier
US8646446B2 (en) 2008-10-01 2014-02-11 Oriel Therapeutics, Inc. Dry powder inhalers with rotating piercing mechanisms and related devices and methods
US8741891B1 (en) 2010-06-22 2014-06-03 Demerx, Inc. N-substituted noribogaine prodrugs
US8765737B1 (en) 2010-05-11 2014-07-01 Demerx, Inc. Methods and compositions for preparing and purifying noribogaine
US8802832B2 (en) 2010-06-22 2014-08-12 Demerx, Inc. Compositions comprising noribogaine and an excipient to facilitate transport across the blood brain barrier
US8859764B2 (en) 2011-01-26 2014-10-14 Demerx, Inc. Methods and compositions for preparing noribogaine from voacangine
US8877921B2 (en) 2012-01-25 2014-11-04 Demerx, Inc. Synthetic voacangine
US8887722B2 (en) 2008-09-26 2014-11-18 Oriel Therapeutics, Inc. Inhaler mechanisms with radially biased piercers and related methods
US8940728B2 (en) 2012-12-20 2015-01-27 Demerx, Inc. Substituted noribogaine
US9045481B2 (en) 2012-12-20 2015-06-02 Demerx, Inc. Substituted noribogaine
US9050427B2 (en) 2008-09-30 2015-06-09 Oriel Therapeutics, Inc. Dry powder inhalers with multi-facet surface deagglomeration chambers and related devices and methods
US9051343B2 (en) 2011-12-09 2015-06-09 Demerx, Inc. Phosphate esters of noribogaine
US9150584B2 (en) 2012-01-25 2015-10-06 Demerx, Inc. Indole and benzofuran fused isoquinuclidene derivatives and processes for preparing them
US9358237B2 (en) 2010-07-23 2016-06-07 Demerx, Inc. Noribogaine compositions
US9394294B2 (en) 2010-05-11 2016-07-19 Demerx, Inc. Methods and compositions for preparing and purifying noribogaine
US9550789B2 (en) 2014-06-18 2017-01-24 Demerx, Inc. Halogenated indole and benzofuran derivatives of isoquinuclidene and processes for preparing them
US9586954B2 (en) 2010-06-22 2017-03-07 Demerx, Inc. N-substituted noribogaine prodrugs
US9617274B1 (en) 2011-08-26 2017-04-11 Demerx, Inc. Synthetic noribogaine
US9783535B2 (en) 2012-12-20 2017-10-10 Demerx, Inc. Substituted noribogaine

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1036562A1 (fr) * 1997-12-03 2000-09-20 Fujisawa Pharmaceutical Co., Ltd. Medicament en pastilles souples et procede de fabrication

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EP0407028B1 (fr) * 1989-05-31 1994-09-14 FISONS plc Formule médicamenteuse et appareil d'inhalation

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Cited By (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4429707C1 (de) * 1994-08-04 1996-02-01 Bernhard Dipl Ing Hugemann Inhalator mit integrierter, verfestigter, ringförmiger Wirkstofftablette
US7601336B2 (en) 1997-06-13 2009-10-13 Chiesi Farmaceutici S.P.A. Pharmaceutical aerosol composition
US8420058B2 (en) 1997-06-13 2013-04-16 Chiesi Farmaceutici S.P.A. Pharmaceutical aerosol composition
US7220737B1 (en) 1997-09-04 2007-05-22 Novoneuron, Inc Noribogaine in the treatment of pain and drug addiction
US8178524B2 (en) 1997-09-04 2012-05-15 Demerx, Inc. Noribogaine in the treatment of pain and drug addiction
US7754710B2 (en) 1997-09-04 2010-07-13 Novoneuron, Inc. Noribogaine in the treatment of pain and drug addiction
WO1999029432A1 (fr) * 1997-12-05 1999-06-17 Palas Gmbh Procede et dispositif pour la production d'un aerosol solide
WO1999061003A1 (fr) * 1998-05-27 1999-12-02 Euroceltique S.A. Systeme de presentation de medicament comprenant de la matiere medicamenteuse solide fortement compactee
US7347199B1 (en) 1998-11-25 2008-03-25 Chiesi Farmaceutici S.P.A. Pressurised metered dose inhalers (MDI)
US8142763B2 (en) 1998-11-25 2012-03-27 Chiesi Farmaceutici S.P.A. Pressurized metered dose inhalers (MDI) containing a solution comprising ipratropium bromide, HFA propellant, and co-solvent and comprising a container with a specific internal surface composition and/or lining
US7223381B2 (en) 1998-11-25 2007-05-29 Chiesi Farmaceutici S.P.A. Pressurised metered dose inhalers (MDI)
US7468194B1 (en) 1999-05-27 2008-12-23 Euro-Celtique, S.A. Preparations for the application of anti-inflammatory agents
US7297344B1 (en) 1999-05-27 2007-11-20 Euro-Celtique, S.A. Preparations for the promotion of wound healing in the upper respiratory tract and/or ear
US7300667B1 (en) 1999-05-27 2007-11-27 Euro-Celtique, S.A. Preparations for the application of anti-inflammatory, especially antiseptic agents and/or agents promoting the healing of wounds, to the lower respiratory tract
US6967017B1 (en) 1999-07-23 2005-11-22 Chiesi Farmaceutici S.P.A. Formulations of steroid solutions for inhalatory administration
US6964759B2 (en) 2000-02-22 2005-11-15 Chiesi Farmaceutici S.P.A. Formulations containing an anticholinergic drug for the treatment of chronic obstructive pulmonary disease
EP1941868A2 (fr) 2000-02-28 2008-07-09 PharmaKodex Limited Améliorations portant sur ou en relation avec l'administration orale de médicaments
WO2001085174A1 (fr) * 2000-05-12 2001-11-15 Chiesi Farmaceutici S.P.A. Formulations contenant un medicament a base de glucocorticoides destinees au traitement des maladies broncho-pulmonaires
US7018618B2 (en) 2000-05-22 2006-03-28 Chiesi Farmaceutici S.P.A. Stable pharmaceutical solution formulations for pressurized metered dose inhalers
US7696178B2 (en) 2001-07-02 2010-04-13 Chiesi Farmaceutici S.P.A. Optimised formulation of tobramycin for aerosolization
US7939502B2 (en) 2001-07-02 2011-05-10 Chiesi Farmaceutici S.P.A. Optimised formulation of tobramycin for aerosolization
US8168598B2 (en) 2001-07-02 2012-05-01 Chiesi Farmaceutici S.P.A. Optimised formulation of tobramycin for aerosolization
US7381402B2 (en) 2004-02-27 2008-06-03 Chiesi Farmaceutici S.P.A. Stable pharmaceutical solution formulations for pressurized metered dose inhalers
DE102005028696A1 (de) * 2005-06-21 2006-12-28 Pulmotec Gmbh Verwendung eines Hilfsstoffs zur Einstellung der Abrasionsfestigkeit eines verfestigten Wirkstoffpräparats
US8550071B2 (en) 2008-09-26 2013-10-08 Oriel Therapeutics, Inc. Inhalers with airway disks having discrete airway channels and related disks and methods
US8985103B2 (en) 2008-09-26 2015-03-24 Oriel Therapeutics, Inc. Dry powder inhalers with dual piercing members
US10493222B2 (en) 2008-09-26 2019-12-03 Oriel Therapeutics, Inc. Dry powder dose container assemblies and related inhalers
US8671938B2 (en) 2008-09-26 2014-03-18 Oriel Therapeutics, Inc. Inhalers with airway disks having discrete airway channels and related disks and methods
US9795749B2 (en) 2008-09-26 2017-10-24 Oriel Therapeutics, Inc. Dry powder inhalers with dual piercing members and methods of operating same
US8381721B2 (en) 2008-09-26 2013-02-26 Oriel Therapeutics, Inc. Dry powder inhalers with dual piercing members and related devices and methods
US9597465B2 (en) 2008-09-26 2017-03-21 Oriel Therapeutics, Inc. Methods of operating and fabricating inhalers with airway disks having discrete airway channels
US8887722B2 (en) 2008-09-26 2014-11-18 Oriel Therapeutics, Inc. Inhaler mechanisms with radially biased piercers and related methods
US9050427B2 (en) 2008-09-30 2015-06-09 Oriel Therapeutics, Inc. Dry powder inhalers with multi-facet surface deagglomeration chambers and related devices and methods
US8646446B2 (en) 2008-10-01 2014-02-11 Oriel Therapeutics, Inc. Dry powder inhalers with rotating piercing mechanisms and related devices and methods
US8362007B1 (en) 2010-05-11 2013-01-29 Demerx, Inc. Substituted noribogaine
US8765737B1 (en) 2010-05-11 2014-07-01 Demerx, Inc. Methods and compositions for preparing and purifying noribogaine
US9394294B2 (en) 2010-05-11 2016-07-19 Demerx, Inc. Methods and compositions for preparing and purifying noribogaine
US8802832B2 (en) 2010-06-22 2014-08-12 Demerx, Inc. Compositions comprising noribogaine and an excipient to facilitate transport across the blood brain barrier
US8637648B1 (en) 2010-06-22 2014-01-28 Demerx, Inc. Compositions comprising noribogaine and an excipient to facilitate transport across the blood brain barrier
US8741891B1 (en) 2010-06-22 2014-06-03 Demerx, Inc. N-substituted noribogaine prodrugs
US9308272B2 (en) 2010-06-22 2016-04-12 Demerx, Inc. Compositions comprising noribogaine and an excipient to facilitate transport across the blood brain barrier
US9586954B2 (en) 2010-06-22 2017-03-07 Demerx, Inc. N-substituted noribogaine prodrugs
US9358237B2 (en) 2010-07-23 2016-06-07 Demerx, Inc. Noribogaine compositions
US9403817B2 (en) 2011-01-26 2016-08-02 Demerx, Inc. Methods and compositions for preparing noribogaine from voacangine
US8859764B2 (en) 2011-01-26 2014-10-14 Demerx, Inc. Methods and compositions for preparing noribogaine from voacangine
US9617274B1 (en) 2011-08-26 2017-04-11 Demerx, Inc. Synthetic noribogaine
US9051343B2 (en) 2011-12-09 2015-06-09 Demerx, Inc. Phosphate esters of noribogaine
US9469649B2 (en) 2012-01-25 2016-10-18 Demerx, Inc. Synthetic voacangine
US8877921B2 (en) 2012-01-25 2014-11-04 Demerx, Inc. Synthetic voacangine
US9150584B2 (en) 2012-01-25 2015-10-06 Demerx, Inc. Indole and benzofuran fused isoquinuclidene derivatives and processes for preparing them
US9045481B2 (en) 2012-12-20 2015-06-02 Demerx, Inc. Substituted noribogaine
US9783535B2 (en) 2012-12-20 2017-10-10 Demerx, Inc. Substituted noribogaine
US8940728B2 (en) 2012-12-20 2015-01-27 Demerx, Inc. Substituted noribogaine
US9550789B2 (en) 2014-06-18 2017-01-24 Demerx, Inc. Halogenated indole and benzofuran derivatives of isoquinuclidene and processes for preparing them

Also Published As

Publication number Publication date
JPH06339513A (ja) 1994-12-13
AU4066693A (en) 1994-07-19

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