throbber
Canadian
`(19) • • •
`Intellectual Property
`Office
`
`Office de la Propriete
`lntellectuelle
`du Canada
`
`(11) CA 2 274 910
`(43) 25.06.1998
`
`(13) A1
`
`An Agency of
`Industry Canada
`
`Un organisme
`d'lndustrie Canada
`
`(12)
`
`(21) 2 274 910
`
`(22) 14.11.1997
`
`(51) Int. Cl.':
`
`A61 K 031/485, A61 K 009/70
`
`(85) 14.06.1999
`
`(86) PCT/EP97/06369
`
`87 W098/26780
`(72)
`
`CREMER, Karsten (DE).
`LUESSEN, Henrik (DE).
`
`196 52 188.2 DE 16.12.1996
`
`(30)
`
`(71)
`
`(54)
`
`(54)
`
`(57)
`
`L TS LOHMANN THERAPIE-SYSTEME GMBH,
`lrlicher Strasse 55
`D-56567, NEUWIED, XX (DE).
`
`(74)
`
`Orange Chari Pillay
`
`PREPARATION MEDICAMENTEUSE PLATE POUR ADMINISTRER OU LIBERER, DANS LA CAVITE
`BUCCALE, DE LA BUPRENORPHINE OU UNE SUBSTANCE COMPARABLE SUR LE PLAN
`PHARMACOLOGIQUE ET PROCEDE PERMETTANT DE LA PREPARER
`FLAT MEDICAMENT PREPARATION FOR THE APPLICATION AND RELEASE OF BUPRENORPHINE OR A
`PHARMACOLOGICALLY COMPARABLE SUBSTANCE IN THE BUCCAL CAVITY, AND METHOD OF
`PRODUCING THE SAME
`
`invention concerns a solid medicament
`The
`preparation which can decompose in aqueous media and
`flat-,
`foil-, paper- or wafer-type presentation
`has a
`for the application and release of active substances in
`the buccal cavity. The
`invention
`is characterized
`in
`that
`it contains buprenorphine, an active substance
`which
`is pharmacologically comparable
`thereto, or a
`therapeutically suitable salt of buprenorphine or of
`the pharmacologically comparable active substance.
`
`DRL - EXHIBIT 1006
`DRL001
`
`

`
`CI P 0
`
`02) (19) ccA) Demande-Application
`
`CANADIAN IKTELLECTUAL
`
`PROPERTY OFFICE
`
`(21)(Al) 2,274,910
`(86) 1997/11/14
`(87) 1998/06/25
`
`0 PI C
`
`OFFICE DE LA PROPRIETE
`
`INTELLECTUELLE DC CANADA
`
`(72) CREMER, Karsten, DE
`(72) LUESSEN, Henrik, DE
`(71) LIS LOHJVIANN THERAPIE-SYSTEME GMBH, DE
`(51) Int.Cl. 6 A61K 31/485, A61K 9/70
`(30) 1996/12/16 (196 52 188.2) DE
`(54) PREPARATION MEDICAMENTEUSE PLATE POUR
`ADMINISTRER OU LIBERER, DANS LA CA VITE BUCCALE,
`DE LA BUPRENORPHINE OU UNE SUBSTANCE
`COMPARABLE SUR LE PLAN PHARMACOLOGIQUE ET
`PROCEDE PERMETTANT DE LA PREPARER
`(54) FLAT MEDICAMENT PREPARATION FOR THE APPLICATION
`AND RELEASE OF BUPRENORPHINE OR A
`PHARMACOLOGICALLY COMPARABLE SUBSTANCE IN
`THE BUCCALCAVITY,AND METHOD OF PRODUCING THE
`SAME
`
`preparation
`unc
`concemc
`L 'invention
`(57)
`medicamenteuse solide, pouvant se decomposer dans des
`substances aqueuses, it forme galenique plate, de type
`film, papier ou hostie, servant it administrer et :i liberer
`des principes actif clans
`la cavite buccale. Cette
`preparation sc caractcrisc en cc qu'cllc conticnt de la
`buprenorphine, un principe actifs comparable sur le plan
`pharmacologique ii la buprenorphine on un sel de
`buprenorphine ou un sel de la substance comparable sm
`le plan pharmacologique et approprie sur le plan
`thcrapcutique .
`
`invention concerns a solid medicament
`(57) The
`preparation which can decompose in aqueous media and
`has a flat-, foil-, paper- or wafer-type presentation for the
`application and release of active substances in the buccal
`cavity. The invention is characterized in that it contains
`an
`active
`substance which
`1s
`huprcnorphinc,
`pharmacologically
`comparable
`thereto,
`or
`a
`therapeutically suitable salt of buprenorphine or of the
`pharmacologically comparable active substance.
`
`••• lndustrie Canada
`
`Industry Canada
`
`DRL - EXHIBIT 1006
`DRL002
`
`

`
`CA 02274910 1999-06-14
`
`13
`
`ABSTRACT
`
`A solid pharmaceutical preparation, disintegratable in
`aqueous media, with a flat, foil-shaped, paper-shaped or
`wafer-shaped administration form, for application and
`release of active substances in the oral cavity is charac(cid:173)
`terized by a content of buprenorphine, of an active
`substance pharmacologically comparable to buprenorphine, or
`of a therapeutically suitable salt of bruprenorphine or the
`pharmacologically comparable active substance.
`
`DRL - EXHIBIT 1006
`DRL003
`
`

`
`...
`
`CA 02274910 1999-06-14
`
`Flat pharmaceutical preparation for application and release
`of buprenorphine or of a pharmacologically comparable
`substance in the oral cavity, and process for the
`production thereof
`
`The present invention relates to a pharmaceutical
`preparation for application of buprenorphine or
`pharmacologically comparable active substances in the
`region of the oral cavity, respectively the oral mucosa.
`More particularly, it relates to a preparation that is
`adapted to be flat and in the form of a foil-, paper- or
`wafer-shaped administration form.
`
`Flat active substance carriers have already been developed
`and produced for various purposes. DE-OS 27 46 414 can be
`regarded as fundamental to this administration form, said
`document describing a foil-type tape of active substance,
`binder and further active substances, with a direct
`relation existing, by reason of the homogeneous thickness,
`density and width, between a unit of length of the tape and
`the dose of active substance contained therein. The
`advantages of the continuous dosage property have been
`recognized also by other applicants and have been described
`in specific individual variants. Thus, DE-PS 36 30 603
`claims a flat-shaped carrier material, for example in the
`form of a separating layer, with an active substance(cid:173)
`containing coating, the latter being peelable, in doses,
`off the carrier material after having been previously
`separated into dosage units.
`
`The practicability of the flat format in general and the
`advantages afforded in the manufacture of the adminis(cid:173)
`tration form and in the dosing when employing such
`administration form have been recognized in the prior art.
`
`DRL - EXHIBIT 1006
`DRL004
`
`

`
`CA 02274910 1999-06-14
`
`2
`
`Moreover, further advantages of such administration forms
`can be derived such as the fact that, relative to the
`weight of the administration form, a relatively large
`surface may be printed on the said administration form,
`thereby making it possible to increase intake safety, as
`well as affording the possibility of discrete intake
`without any liquid being available.
`
`Despite these obvious advantages, such flat administration
`forms have hitherto hardly been successful. Obviously, the
`advantage as compared to conventional administration forms
`does not suffice for many manufacturers of pharmaceutics to
`develop products of this type comprising the usual active
`ingredients and to pursue the legal drug approval thereof.
`Moreover, existing production machinery and existing know(cid:173)
`how cannot be made use of for these novel products; this
`means that the necessity of large investments would arise.
`Despite the above-described advantages of flat, film- or
`paper-like administration forms, the therapeutic and/or
`economic advantage in administration of common active
`substances which are also perorally applicable is
`apparently not great enough as compared to conventional
`tablets to justify the costs of switching over to these
`administration forms.
`
`One of the substances that are little suitable for peroral
`administration is buprenorphine, an opiate which has been
`successfully used in the therapy of pain for years. After
`peroral application it is hardly bioavalable, i.e. it
`appears in the blood circulation only to the very small
`extent of a few percent of the dose taken (McQuay & Moore,
`in: Bupenorphine, ed. Cowan & Lewis, New York 1995).
`Presumably, the reason for the lack in bioavailability lies
`in the extensive decomposition of the substance during the
`first liver passage following gastrointestinal absorption
`("first-pass effect"). A possibility of avoiding the first-
`
`DRL - EXHIBIT 1006
`DRL005
`
`

`
`CA 02274910 1999-06-14
`
`3
`
`pass effect in oral administration is to bring the active
`substance to absorption already on the oral mucosa. In
`order to enter the central systemic circulation, an active
`substance which enters into the blood via the oral mucosa
`does not have to first pass the portal system and thus, in
`concentrated form, the liver, which metabolizes the active
`substance. A prerequisite for buccal or sublingual
`application, however, is a sufficient permeability of the
`oral mucosa to the active substance, taking into
`consideration the required dose. Permeability in turn
`depends to a large extent on the physicochemical properties
`of the active substance. Since buprenorphine is effective
`in very small doses, and since it has the required
`physicochemical characteristics, buccal or sublingual
`application is very attractive.
`
`In fact, apart from injectable administration forms there
`are - at least in Germany - no commercially available
`peroral administration forms, but only so-called sublingual
`tablets, which comprise buprenorphine (Temgesic® sub(cid:173)
`lingual). It is true that such tablets take into account
`the fact that sublingual application of the active
`substance is preferable to peroral administration - even
`though they do so above all by way of their intake
`directions as only these suggest the sublingual
`administration, not the tablet itself. However, they offer
`a vehicle which has considerable drawbacks for this purpose
`of application. Among these disadvantages is, firstly, the
`not inconsiderable disintegration time, which in the case
`of pressed tablets is at least several minutes even under
`favorable conditions, and in the case of the commercially
`available tablets is typically about 5 to 10 minutes. For
`patients suffering from severe, acute pain this
`disintegration time results in an unwanted delay of the
`onset of action; in a substitution or withdrawal therapy,
`however, this puts a strain on the medicinal personnel with
`
`DRL - EXHIBIT 1006
`DRL006
`
`

`
`CA 02274910 1999-06-14
`
`4
`
`respect to the time required for administration, since the
`personnel must supervise that the tablets are used as
`directed and must prevent improper removal of the non(cid:173)
`disintegrated tablet from the mouth. Further disadvantages
`of the tablet are the foreign body sensation occurring
`during the disintegration time, but also the great
`variability in the extent of sublingual absorption, which
`is caused by the active substance during or after
`disintegration of the tablet having for the most part no
`direct contact with the oral mucosa, but being released
`into the saliva; the saliva, however, can be retained in
`the oral cavity for a very variable time, which is more or
`less haphazard, before being swallowed.
`
`It is thus the object of the present invention to create
`pharmaceutical preparations based on, and having the
`general advantages of, flat, film-like or paper-like active
`substance carriers which by reason of the combination with
`a special active substance have additional economical
`and/or therapeutical advantages, apart from those mentioned
`above, over pharmaceutical preparations of the same active
`substance based on conventional administration forms such
`as tablets. In addition, it is likewise an object of the
`invention to provide an administration form for
`buprenorphine that releases the active substance in the
`oral cavity while not having the disadvantages described in
`the prior art.
`
`The object is achieved in accordance with the features of
`the claims by providing an administration form on the basis
`of a flat, foil-, paper- or wafer-like active substance
`carrier, which administration form contains as active
`substance buprenorphine, respectively one of its
`therapeutically acceptable salts, or a therapeutically
`comparable active substance. As will be eXPlained in the
`following, an administration form according to Claim l is
`
`DRL - EXHIBIT 1006
`DRL007
`
`

`
`CA 02274910 1999-06-14
`
`5
`
`by far superior to a conventional administration form for
`administering buprenorphine - both from the economical as
`well as the therapeutical point of view - and it is
`especially suitable, on the one hand, for analgesia in
`cases of acute conditions of pain, and, on the other hand,
`for the therapy of opiate or cocaine addiction in the sense
`of a substitution therapy or a withdrawal program..
`
`The pharmaceutical preparation according to claim 1 can,
`upon application, be brought into direct contact with the
`oral mucosa. Due to the flat design, immediately after
`application about half of the surf ace of the administration
`form, which is large anyway, is located directly on the
`mucosa. The buprenorphine released thus encounters two
`factors particularly favorable for entry into the body,
`namely a short diffusion path and a large diffusion area.
`This reduces the portion of buprenorphine that is
`swallowed, which in the case of many other active agents
`would not be a particular problem. However, with
`buprenorphine, swallowing of the active substance should be
`avoided if possible, or should be reduced since, for the
`above mentioned reasons, swallowed buprenorphine is
`ineffective. Even in the case of the most simple embodiment
`according to the invention, and given a disintegration time
`of a few minutes following application or following
`introduction into aqueous media, the superiority of a
`buprenorphine-containing film over a buprenorphine(cid:173)
`containing tablet will thus become evident.
`
`An improved contact of the pharmaceutical preparation with
`the oral mucosa can be achieved through selecting auxiliary
`substances. It is known of certain orally applicable
`auxiliary agents which are commonly used in pharmaceutics
`that they have mucoadhesive properties. Examples for such
`mucoadhesive substances are polyacrylic acid, carboxy(cid:173)
`methylcellulose, tragacanth, alginic acid, gelatin,
`
`DRL - EXHIBIT 1006
`DRL008
`
`

`
`CA 02274910 1999-06-14
`
`6
`
`hydroxymethylcellulose, methylcellulose and gum arabic. In
`addition, it is known of various non-mucoadhesive
`substances that in certain mixing ratios they develop
`mucoadhesive properties too. An example for such a mixture
`is glycerol monooleate/water in a ratio of 84:16 (Engstrom
`et al., Pharm. Tech. Eur. 7 [1995], No. 2, pages 14-17).
`
`In the case that mucoadhesive auxiliary substances are
`used, it is preferable for the administration form of the
`pharmaceutical preparation according to the invention to
`have a two-layer or multi-layer structure. It can thereby
`be prevented that the preparation conglutinates various
`parts of the mucosa with each other, which would lead to
`sensations of considerable discomfort during application.
`In addition, it is in such a case preferable for the
`administration form to have a structure the non(cid:173)
`mucoadhesi ve layer of which has a permeability to the
`active substance which is relatively smaller than that of
`the mucoadhesive layer, it thereby being possible to
`prevent that active substance losses occur due to active
`substance being released into the saliva instead of to the
`mucosa.
`
`Pharmaceutical preparations according to the present
`invention are also those containing, apart from the active
`substance buprenorphine or an active substance
`pharmacologically comparable thereto, one or more further
`active substances. Such a preparation can be advantageous
`in several respects. On the one hand it is a recognized
`method for treating several symptoms or conditions
`occurring simultaneously to administer a fixed active
`substance combination in a medicament. To this end, it is
`possible to incorporate any therapeutically appropriate
`active substances into the preparation according to the
`present invention. On the other hand, the combination, as
`according to the invention, of an opiate active substance
`
`DRL - EXHIBIT 1006
`DRL009
`
`

`
`CA 02274910 1999-06-14
`
`7
`
`with another substance that is capable of reducing the
`specific risks of opiate administration is especially
`useful and advantageous.
`Thus - possibly partial - opiate antagonists, such as, for
`example, nalbuphine, naloxone or naltrexone, can be
`combined with the opiate active substance, which results in
`the risk of addiction or habituation involved in the
`repeated administration of the preparation being diminished
`by reason of the fact that the dose cannot be increased
`without at the same time accepting an increase of the
`antagonistic effect. The success of this strategy will
`depend on the selection of a suitable antagonist as well as
`the selection of the dose ratio.
`
`Though buprenorphine - optionally in the form of one of its
`therapeutically acceptable salts -
`is the most preferred
`active substance, the invention also relates to such active
`substances as are pharmacologically similar or comparable
`to buprenorphine since the advantages of the invention
`described herein also apply in these cases, though to
`different extent. Further suitable active substances, which
`are also described herein as being "pharmacologically
`similar or comparable", are, in particular, those
`substances belonging to the opiates or opioids since many
`of these not only exhibit pharmacodynamic but also
`pharmacokinetic similarities to buprenorphine, that is a
`relatively low dose, good capacity for permeating
`membranes, and a high first-pass effect. Particularly
`preferred are morphine derivatives or dihydromorphine
`derivatives as well as substances from the methadone and
`fentanyl group.
`
`In order not to promote any improper application or one
`that does not conform to the intended use, pharmaceutical
`preparations according to the invention will typically be
`present predivided into doses and separated from each other
`
`DRL - EXHIBIT 1006
`DRL010
`
`

`
`CA 02274910 1999-06-14
`
`8
`
`in a suitable package, so that when removing a dosage unit
`it will be possible to remove only one unit at a time, such
`as in the case of a blister pack, where each dosage unit is
`sealed individually in a deep-drawn cup. Within programs
`for treatment of opiate or cocaine addiction it may,
`however, also be useful to supply physicians who are
`providing the medical care, for example, with preparations
`in the form of packaging units wherein said preparations
`are present as undivided sheet-like or tape-like material,
`from which the dosage units can be separated for the
`purpose of application. This facilitates mass application
`and affords the physicians who are administering the
`preparations the possibility of separating from one and the
`same material various dosage units in accordance with the
`given dosage requirements.
`
`Since the pharmaceutical preparation according to the
`present invention is expected to exhibit increased bio(cid:173)
`availability as compared to known preparations, it will
`possibly be necessary to adjust the dosage. In tbe case of
`buprenorpbine the individual analgesic dose will be about
`0.1 to 1 mg; in addiction or substitution therapy, however,
`this value might be considerably higher.
`In accordance with the invention the manufacture of the
`pharmaceutical preparation is performed in several steps.
`For preparing the web-shaped starting material -
`from which
`ultimately either individual doses or entire packaging
`units will be separated by cutting or punching -
`two basic
`process variants are suitable. The first group of processes
`includes those where a tape, or a process sheet or foil, is
`evenly coated with aqueous or solvent-containing liquids
`being in part of higher viscosity, and where this is
`subsequently subjected to a drying process. To this end,
`first, a coating mass is prepared, for which purpose at
`least one water-soluble polymer capable of forming a film,
`the active substance(s) and a suitable, vaporizable liquid
`
`DRL - EXHIBIT 1006
`DRL011
`
`

`
`CA 02274910 1999-06-14
`
`9
`
`must be intimately mixed. If required it is possible to
`incorporate further auxiliary substances such as
`disintegration-modifying polymers, softeners, fillers,
`texture-providing substances, pigments, dyes, taste
`corrigents, solubilizers, substances for adjusting the pH,
`*smoothing agents, dulling agents, disintegration
`promoters, etc. As an alternative, the web-like starting
`material may be made by thermoplastic forming, i.e. without
`the aid of liquids. suitable processes are, inter alia, any
`hot-melt coating methods as well as any extrusion methods.
`As a prerequisite, the polymer or polymer mixture capable
`of film-formation must in this case be thermoplastically
`formable. The required ingredients are mixed and, under
`action of pressure and/or heat, formed by extruding,
`blowing or by coating of tapes, sheets or foils, and, after
`solidification, transferred for further processing.
`Suitable for the manufacture of preparations according to
`the present invention that have a multi-layer structure are
`correspondingly modified methods, it being irrelevant
`whether several web-shaped materials are simultaneously or
`subsequently produced and combined.
`
`DRL - EXHIBIT 1006
`DRL012
`
`

`
`CA 02274910 1999-06-14
`
`10
`
`C L A I M S
`
`1. Buccal pharmaceutical preparation for treating acute
`conditions of pain or for addiction therapy, comprising as
`active substance buprenorphine or a pharmacologically
`comparable substance as such or as a therapeutically
`suitable salt, characterized by a wafer-shaped adminis(cid:173)
`tration form, disintegratable in the aqueous medium of the
`oral cavity, which has a mucoadhesive, active substance(cid:173)
`containing layer based on water-soluble, film-forming
`polymers of small thickness, for rapid active substance
`transfer through short diffusion paths, while having a
`large surface appropriate to the effective dose.
`
`Pharmaceutical preparation according to claim 1,
`2.
`characterized by a mono- or multi-layered structure having
`a mucoadhesive active substance-containing layer based on
`water-soluble, film-forming polymers of small thickness for
`rapid active substance uptake through short diffusion
`paths.
`
`Pharmaceutical preparation according to claim 1 or 2,
`3.
`characterized by a non-mucoadhesive outer layer, opposed to
`the mucoadhesive surface, which outer layer has a lower
`permeability to the active substance.
`
`4. Pharmaceutical preparation according to any one of the
`preceding claims, characterized by a single-dose
`buprenorphine content of 0.1 - 1 mg.
`
`Pharmaceutical preparation according to any one of the
`5.
`preceding claims, characterized in that it is equipped with
`bioadhesive or mucoadhesive properties by the addition of
`an adhesion-promoting auxiliary substance or auxiliary
`substance mixture.
`
`DRL - EXHIBIT 1006
`DRL013
`
`

`
`CA 02274910 1999-06-14
`
`11
`
`Pharmaceutical preparation according to claim 5,
`6.
`characterized in that further active substance is present
`which is suitable for treating addiction to opiates.
`
`Pharmaceutical preparation according to claim 6,
`7.
`characterized in that further active substance is, at least
`partially, capable of opiate antagonist action.
`
`Pharmaceutical preparation according to claim 7,
`8.
`characterized in that it contains nalbuphine, naloxone or
`naltrexone.
`
`Pharmaceutical preparation according to one or more of
`9.
`the preceding claims, characterized in that it is present
`as an undivided, sheet-shaped or tape-shaped material, from
`which it is possible to separate dosage units for the
`purpose of application.
`
`10. Pharmaceutical preparation according to one or more of
`the preceding claims, characterized in that it is present
`predivided into doses.
`
`11. Pharmaceutical preparation according to one or more
`of the preceding claims, characterized in that, per dosage
`unit, it has a content of active substance which is
`suitable for analgesia.
`
`12. Pharmaceutical preparation according to one or more of
`the preceding claims, characterized in that, per dosage
`unit, it has a content of active substance which is
`suitable for opiate or cocaine substitution therapy.
`
`13. Method of producing a pharmaceutical preparation
`according to one or more of the preceding claims,
`
`DRL - EXHIBIT 1006
`DRL014
`
`

`
`CA 02274910 1999-06-14
`
`12
`
`characterized in that in a first step the active sub(cid:173)
`stance Cs), together with a water-soluble polymer capable of
`film-formation, is (are) dissolved in a suitable,
`hydrophile solvent, optionally in presence of further
`dissolved or suspended auxiliary agents, that in a second
`step the solution or suspension is applied, in a continuous
`process and with even thickness, to a tape or a process
`sheet or foil, where, in a third step, it is largely freed
`from the solvent, thereby forming a sheet-shaped or tape(cid:173)
`shaped starting material, wherefrom, in a fourth step, the
`dosage or multidosage units are separated by cutting or
`punching.
`
`14. Method of producing a pharmaceutical preparation
`according to one or more of the preceding claims,
`characterized in that in a first step the active sub(cid:173)
`stance (s), together with a water-soluble, thermoplastic
`polymer capable of film-formation, is (are) formed, under
`action of heat and/or pressure, and optionally in presence
`of further auxiliary substances, into a sheet-shaped or
`tape-shaped starting material, from which starting material
`the dosage or multidosage units are separated by cutting or
`punching.
`
`15. Method of producing a pharmaceutical preparation
`according to claim 13 or 14, characterized in that a
`plurality of simultaneously or subsequently prepared,
`sheet-shaped or tape-shaped starting materials are combined
`to form a multilayered material, from which the dosage or
`multidosage units are separated.
`
`DRL - EXHIBIT 1006
`DRL015

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