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Patent 2092074 Summary

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(12) Patent: (11) CA 2092074
(54) English Title: RAPIDLY DISINTEGRATABLE MULTIPARTICULATE TABLET
(54) French Title: TABLETTE MULTIPARTICULEE A DESINTEGRATION RAPIDE
Status: Expired
Bibliographic Data
(51) International Patent Classification (IPC):
  • A61K 9/20 (2006.01)
  • A61K 9/00 (2006.01)
(72) Inventors :
  • COUSIN, GERARD (France)
  • BRUNA, ETIENNE (France)
  • GENDROT, EDOUARD (France)
(73) Owners :
  • ETHYPHARM (France)
(71) Applicants :
(74) Agent: GOWLING LAFLEUR HENDERSON LLP
(74) Associate agent:
(45) Issued: 1998-05-19
(86) PCT Filing Date: 1992-07-21
(87) Open to Public Inspection: 1993-01-23
Examination requested: 1995-10-20
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/FR1992/000715
(87) International Publication Number: WO1993/001805
(85) National Entry: 1993-03-19

(30) Application Priority Data:
Application No. Country/Territory Date
91 09245 France 1991-07-22

Abstracts

English Abstract






Rapidly disintegratable multiparticulate tablet
the excipient mixture of which is suitable for imparting a
disintegration rate such that the tablet disintegrates in
the mouth in an extremely short time, notably in less than
sixty seconds, characterized by the fact that the active
substance is present in the form of coated microcrystals
or coated or uncoated microgranules.


French Abstract

Un comprimé multiparticulaire facilement désintégrable dont le mélange d'excipients confère un taux de désintégration tel que les comprimés se désintègrent dans la bouche dans un temps extrêmement court, à savoir en moins de soixante secondes; le comprimé se caractérise par le fait que le principe actif est présent sous forme de microcristaux enrobés ou de microgranules enrobés ou non enrobés.

Claims

Note: Claims are shown in the official language in which they were submitted.


THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A rapidly disintegratable tablet for oral
administration with or without the use of water, said
tablet comprising an active substance and a mixture of
excipients, wherein said active substance is multiparticulate
and in the form of coated microcrystals, coated
microgranules or uncoated microgranules and wherein said
mixture of excipients comprises excipients which are
responsible for the disintegration, said tablet being
intended to be swallowed, said disintegration occuring in
less than sixty seconds under the action of the excipients
which are responsible for the disintegration and which are
selected from the group consisting at least one disintegrating
agent and at least one swelling agent.

2. The tablet of claim 1, wherein the active
substance is in the form of coated microcrystals and is
selected from the group consisting of gastrointestinal
sedatives, antacids, analgesics, anti-inflammatory agents,
coronary vasodilators, peripheral and brain-vasodilators,
anti-infectious agents, antibiotics, antiviral agents,
antiparasitic agents, anticancerous drugs, antianxiety
agents, neuroleptic drugs, agents stimulating the central
nervous system, antidepressant drugs, antihistaminic
agents, antidiarrheal agents, laxatives, nutritional
supplements, immunodepressant drugs, cholesterol lowering
agents, hormones, enzymes, antispasmodic agents, antiangorous
agents, drugs acting on the rhythm of the heart,
drugs used in the treatment of arterial hypertension,
anti-migraine agents, drugs acting on blood coagulability,
antiepileptic agents, myorelaxing agents, drugs used
in the treatment of diabetes, drugs used in the treatment
of thyroidal dysfunctions, diuretical agents, anorexigenic
drugs, antiasthmatic agents, expectorants, antitussive
agents, mucoregulators, decongestants, hypnotics,
anti-nausea agents, hematopoietical agents, uricosuric agents,
plant extracts and contrast mediums.



3. The tablet of claim 1, wherein the active
substance is in the form of coated microgranules and is
selected from the group consisting of gastrointestinal
sedatives, antacids, analgesics, anti-inflammatory agents,
coronary vasodilators, peripheral and brain-vasodilators,
anti-infectious agents, antibiotics, antiviral agents,
antiparasitic agents, anticancerous drugs, antianxiety
agents, neuroleptic drugs, agents stimulating the central
nervous system, antidepressant drugs, antihistaminic
agents, antidiarrheal agents, laxatives, nutritional
supplements, immunodepressant drugs, cholesterol lowering
agents, hormones, enzymes, antispasmodic agents, antiangorous
agents, drugs acting on the rhythm of the heart,
drugs used in the treatment of arterial hypertension,
anti-migraine agents, drugs acting on blood coagulability,
antiepileptic agents, myorelaxing agents, drugs used in
the treatment of diabetes, drugs used in the treatment of
thyroidal dysfunctions, diuretical agents, anorexigenic
drugs, antiasthmatic agents, expectorants, antitussive
agents, mucoregulators, decongestants, hypnotics, antinausea
agents, hematopoietical agents, uricosuric agents,
plant extracts and contrast mediums.

4. The tablet of claim 1, wherein the mixture of
excipients comprises at least one disintegrating agent
selected from the group consisting of carboxymethylcellulose,
insoluble reticulated PVP type and at least one
swelling agent selected from the group consisting of
starch, modified starch and microcrystalline cellulose.

5. The tablet of claim 1, wherein the mixture of
excipients comprises at least one disintegrating agent
selected from the group consisting of carboxymethylcellulose,
insoluble reticulated PVP, at least one swelling
agent selected from the group consisting of starch,
modified starch, microcrystalline cellulose and a direct
compression sugar.



6. The tablet of claim 1, wherein the active
substance is in the form of uncoated microgranules and is
selected from the group consisting of gastrointestinal
sedatives, antacids, analgesics, anti-inflammatory agents,
coronary vasodilators, peripheral and brain-vasodilators,
anti-infectious agents, antibiotics, antiviral agents,
antiparasitic agents, anticancerous drugs, antianxiety
agents, neuroleptic drugs, agents stimulating the central
nervous system, antidepressant drugs, antihistaminic
agents, antidiarrheal agents, laxatives, nutritional
supplements, immunodepressant drugs, cholesterol lowering
agents, hormones, enzymes, antispasmodic agents, antiangorous
agents, drugs acting on the rhythm of the heart,
drugs used in the treatment of arterial hypertension,
anti-migraine agents, drugs acting on blood coagulability,
antiepileptic agents, myorelaxing agents, drugs used
in the treatment of diabetes, drugs used in the treatment
of thyroidal dysfunctions, diuretical agents, anorexigenic
drugs, antiasthmatic agents, expectorants, antitussive
agents, mucoregulators, decongestants, hypnotics,
antinausea agents, hematopoietical agents, uricosuric agents,
plant extracts and contrast mediums.

Description

Note: Descriptions are shown in the official language in which they were submitted.


2~92~7~




RAPIDLY DISINT~GRATABLE MULTIP~RTICULATE TABLET

The invention relates to a rapidly disintegratable
multiparticulate tablet, i.e. a pharmaceutical presenta-
tion for oral administration whose disintegration rate issuch that, when it is placed into the buccal cavity and
particularly on the tongue, it disintegrates in less than
sixty seconds providing with the saliva present a suspen-
sion easy to be swallowed.
The disin~egration rate is obtained due to a
mixture of excipients or vehicles which comprises
generally a disintegrating agent which may consist of a
carboxymethylcellulose and a swelling agent which may
consist of modified starch.
The active substance or principle is mixed with the
abovesaid vehicles, the mixture then being tabletted after
addition of a lubricant such as, for example, magnesium
stearate.
The Applicants have had the merit of having found
that it was possible, unexpectedly and surprisingly, to
introduce into a multiparticulate tablet with high disin-
tegration rate such as hereabove defined, the active
substance in the form of coated or non-coated micro-
crystals or ~icrogranules; thus, the physician has at his
disposal a rapidly disintegratable multiparticulate tablet
proper to facilitate the taking by the patient of most
diversified active substances and especially of those
whose taste is particularly unpleasant, the said tablet
permitting the taking of the said active substances with
as diversified features as gastroresistance and controlled
release due to the fact that the said coated or non-coated
microcrystals and microgranules preserve, after having
been shaped in the form of a multiparticulate tablet,
their initial properties amongst which masking of taste,
gastroresistance and controlled release of the active
principle.

2~2~7~


Consequently, the rapidly disintegratable multipar-
ticulate tablet according to the invention, which can be
used for human beings and for animals, the excipient
mixture of which is such as to provide it with a disinte~
gration rate so that its disintegration in the buccal
cavity occurs in an extremely short time and especially
shorter than sixty seconds, is characterized by the fact
that the active substance is in the form of coated or non-
coated microcrystals or microgranules with modified action
or non-modified action.
According to an advantageous embodiment of the
abovesaid tablet, the mixture of excipients comprises one
or several disintegrating agents of the carboxymethylcel-
lulose type or insoluble reticulated PVP type, one or
several swelling agents which may consist of a carboxy-
methylcellulose, a starch, a modified starch, for instance
a carboxymethylated starch, or a microcrystalline cellu-
lose, and possibly a direct compression sugar consisting
for example of 92% of dextrose.
According to an advantageous embodiment, the
tablets according to the invention, wherein the active
substance is in the ~orm of coated microcrystals, comprise
as active substance at least one of those of the group
comprising the gastrointestinal sedatives, the antacids,
the analgesics, the anti-inflammatory agents, the coronary
vasodilators, the peripheral and brain-vasodilators, the
anti-infectious agents, the antibiotics, the antiviral
agents, the antiparasitic agents, the anticancerous drugs,
the antianxiety agents, the neuroleptic drugs, the agents
stimulating the central nervous system, the antidepressant
drugs, the antihistaminic agents, the antidiarrheal
agents, the laxatives, the nutritional supplements, the
immunodepressant drugs, the cholesterol lowering agents,
the hormones, the enzymes, the antispasmodic agents, the
3~ antiangorous agents, the drugs acting on the rhythm of the
heart, the drugs used in the treatment of arterial hyper-

2~2~7~


tension, the anti-migraine agents, the drugs acting on
blood coagulability, the antiepileptic agents, the
myorelaxing agents, the drugs used in the treatment of
diabetes, the drugs used in the treatment of thyroidal
dysfunctions, the diuretical agents, the anorexigenic
drugs, the antiasthmatic agents, the expectorants, the
antitussive agents, the mucoregulators, the decongestants,
the hypnotics, the antinauseous agents, the hematopoie-
tical agents, the uricosuric agents, the plant extracts,
the contrast mediums.
According to another advantageous embodiment, the
tablets according to the invention, wherein the active
substance is present in the form of coated or non-coated
microgranules with modified action or non-modified action,
comprise as active substance at least one of those of the
group comprising the gastrointestinal sedatives, the
antacids, the analgesics, the anti-inflammatory agents,
the coronary vasodilators, the peripheral and brain-
vasodilators, the anti-infectious agents, the antibiotics,
the antiviral agents, the antiparasitic agents, the anti-
cancerous drugs, the antianxiety agents, the neuroleptic
drugs, the agents stimulating the central nervous system,
the antidepressant drugs, the antihistaminic agents, the
antidiarrheal agents, the laxatives, the nutritional
supplements, the immunodepressant drugs, the cholesterol
lowering agents, the hormones, the enzymes, the anti-
spasmodic agents, the antiangorous agents, the drugs
acting on the rhythm of the heart, the drugs used in the
treatment of arterial hypertension, the anti-migraine
agents, the drugs acting on blood coagulability, the
antiepileptic agents, the myorelaxing agents, the drugs
used in the treatment of diabetes, the drugs used in the
treatment of thyroidal dysfunctions, the diuretical
agents, the anorexigenic clrugs, the antiasthmatic agents,
the expectorants, the antitussive agents, the mucoregu-
lators, the decongestants, the hypnotics, the antinauseous

2092~7A


agents, the hematopoietical agents, the uricosuric agents,
the plant extracts, the contrast mediums.
The use of the tablet according to the invention is
especially advantageous due to the fact that it may be
very easily used by any users. The said tablet can be
taken in any condition (when working, when travelling and
so on), without a glass and without water. It constitutes
an "ambulatory" pharmaceutical presentation which can
advantageously be used instead of numerous pharmaceutical
presentations such as sachets, effervescent tablets,
drinkable ampoules, capsules, traditional tablets and so
on.
Its very easy facility of administration is espe-
cially interesting when it is necessary that young
children or old people take therapeutical substances, i.e.
populations which often have swallowing difficulties, i.e.
populations which keep the drug in the mouth and which are
unable to swallow it. Contrary to the traditional tablet
or to the capsule, the tablet according to the invention
offers in connection with such populations an advantage of
security as, as soon as it is introduced in the mouth, it
provides a therapeutical protection.
On the other hand, it is important to emphasize
that, even directly swallowed with a little water for
example, the said tablet preserves its rapid disintegra-
tion rate within the stomach. This type of administration
will again raise no security problem.
Furthermore, the tablet according to the invention
provides a further big advantage with respect to tablets
or simple capsules. In fact until today, people who need
to swallow a tablet or a capsule under the above-mentioned
conditions (during working, during travelling, without
water and without a glass), swallowed the said tablet or
capsule without water and that could be dangerous as the
tablet or capsule can block in the esophagus and provide
thus an important delay as far as absorption of the active

2~2~74


principle is concerned or even an ulceration at the level
of the esophagus. Similarly, the fact that, on the one
hand, the active principle is coated and, on the other
hand, that it is present in the form of a multiparticulate
tablet, prevents agressive active principles causing
ulcerations of the esophagial or gastric mucous membranes,
phenomenon whieh is sometimes caused by certain
pharmaeeutical presentations which are monolithic,
especially when the patient sueeeeds in swallowing them
with a little water or no water.
Another advantage of the tablet aeeording to the
invention is that the said tablet has not the well-known
drawbaeks of effervescent tablets as for instanee the
taste whieh is very unpleasant to the child, the high
sodium content whieh is disturbing to people whieh must
follow a diet without sodium and finally the neeessity of
having water and a glass for its administration.
Furthermore, it permits the formulation of eertain
aetive prineiples which are not adapted to a previous
extraeorporeal dissolution and which eonsequently ean be
eontemplated only under a dry form, whieh prevents their
use in effervescent tablets; consequently, the tablet
aecording to the present invention has all the advantages
of the dry forms, i.e. the stability as well as the
facility of packaging and storage.
On the other hand, this new pharmaceutieal form may
contain if neeessary two or seYeral aetive prineiples
whieh are usually ineompatible with one another and this
without alteration of their stability.
Another advantage of the tablet aecording to the
invention eonsists in the possibility of taking by the
patient o~ doses of aetive prineiple whieh are more
important than in the past. As a matter of fact as the
said tablet is not to be swallowed under its inltial ~orm
but after disintegration within the buccal cavity, its
size might be greater than that of a elassieal

2~ 07~


pharmaceutical form which must be adapted to be swallowed
without disturbing the taking of the drug.
Finally, the tablet according to the invention has
all the advantages of coated particles which permit to
obtain especially a taste-masking, a gastroresistance, a
delayed release as well as all the advantages of the
multiparticulate forms with modified action or non-
modified action, i.e. a great exchange surface, the
dispersion, less inter- and intra-individual variations, a
very reduced gastric empting influence, a very reduced
intestinal transit time influence as well as reduced pH
influence in the digestive tract, reduced influence of the
viscosity and consequently of food and of the position of
the body, without local toxic manifestation.
The preparation of the rapidly disintegratable
multiparticulate tablets according to the invention is as
follows or similar.
When the active principle is in the form of coated
microcrystals, it is possible to proceed as follows.
The microcrystals are coated by way of a process
known by itself such as, for example, the fluidized air
bed, the coacervation and the microencapsulation.
The mixture of excipients is then prepared by the
dry- or wet-granulation method.
Then, the coated microcrystals are mixed under dry
conditions with the mixture of excipients before
compression.
The preparation of the tablet according to the
invention wherein the active principle is in the form of
coated or non-coated microgranules, may be as follows.
The active principle is put in the form of
microgranules by way of a method known by itself such as,
for example, extrusion-spheronisation, manufacture in pan,
fluidized air bed and 50 on.
Once obtained, these microgranules are coated if
ne~essary in a pan or in a fluidized air bed.

2 ~ 3 r'~ ~


The mixture of excipients is then prepared by the
dry- or wet-granulation method.
Then, the coated or non-coated microgranules are
mixed under dry conditions with the mixture of excipients
before compression.
The invention may even be better understood by way
of the following non-limitating examples which relate to
advantageous embodiments of the invention.
EXAMPLE 1
Rapidly disinteqratable multiparticulate tablet based on
coated crystals of paracetamol.
Tablets according to the invention are prepared
whose composition is as follows.
Formula:
coated paracetamol (with 6~ ethylcellulose) . 530 mg
direct compression sugar . . . . . . . . . . 160 mg
microcrystalline cellulose . . . . . . . . . 90 mg
reticulated polyvinylpyrrolidone . . . . . . 60 mg
sodic carboxymethylcellulose . . . . . . . . 50 mg
colloidal silica . . . . . . . . . . . . . . 6 mg
lubricant ..................................... 4 mg
sweetener . . . . . . . . . . . . . . . . . .25 mg
aroma . . . . . . . . . . . . . . . . . . . .15 mg
magnesium trisilicate . . . . . . . . . . .50 mg
Total990 mg
The said tablet is prepared as follows.
The paracetamol crystals are introduced in a
fluidized air bed installation and a solution of ethylcel-
lulose in an ethanol/acetone mixture is sprayed thereon.
The excipients are sieved and the coatedparacetamol is homogeneized with the excipients inside a
mixing device under dry conditions.
Distribution and tabletting are carried out on a
compressing machine fitted with punches having a diameter
equal to 15 mm and a radius of curvature equal to 20 mm.

2 ~ 7 ~ -


The pressure is equal to 16 ~Newtons +1. The
hardness of the thus obtained tablets is equal to 100
Newtons +10. The time of disintegration in the mouth is
from 35 to 45 seconds.
EXAMPLE ~
Rapidly disinteqratable multiparticulate tablet based on
coated cimetidine crystals.
Tablets according to the invention are prepared
whose composition is as follows.
Formula:
coated cimetidine (with 15.25~ of Eudragit E) 944 mg
reticulated polyvinylpyrrolidone . . . . . . 89 mg
magnesium stearate . . . . . . . . . . . . . 5 mg
sweetener . . . . . . . . . , . . . . . . . . 50 mg
aroma . . . . . . . . . . . . . . . . . . . 12 mg

Total1100 mg
The said tablet is prepared as follows.
The cimetidine crystals are introduced in a
fluidized air bed installation and a solution of a
copolymer of dimethyl-aminoethyl-methacrylate and of
neutral esters of methacrylic acid known under the
trademark "Eudragit E" in alcohol is sprayed thereon.
The excipients are sieved and the coated
cimetidine is homogeneized with the excipients inside a
mixing apparatus under dr~ conditions.
Distribution and tabletting are executed on a
compressing machine equipped with punches having a
diameter equal to 16 mm and a radius of curvature equal to
20 mm.
The pressure is 20 KNewtons +1. The hardness of
the thus obtained tablets is 95 Newtons +10. The time of
disintegration in the mouth is from 15 to 20 seconds.



EXAMPLE 3
Rapidly disinteqratable multiparticulate tablet based on
coated crystals of paracetamol.
Tablets according to the invention composed as
follows are prepared.
Formula:
complex of paracetamol-codeine
(30 mg of codeine and 18.4~ of Eudragit~) 627.5 mg
reticulated polyvinylpyrrolidone . . . . 90 mg
sodium carboxymethylcellulose . . . . . . 70 mg
starch commercialized under the trademark
"STARCH 1500" . . . . . . . . . . . . . 100 mg
sweetener ................................. 40 mg
aroma . . . . . . . . . . . . . . . . . . 22.5 mg
Total950 mg
Eudragit is a copolymer of methacrylic acid.
This tablet is prepared as ~ollows.
The crystals of paracetamol are introduced in a
fluidized air bed installation and the codeine dissolved
in a solution of Eudragit E and Eudragit NE 30D (neutral
polymer of esters of polymethacrylic acid) is sprayed
thereon.
The excipients are sieved and the coated
paracetamol is homogeneized with the excipients in a
mixing apparatus under dry conditions.
Distribution and tabletting are carried out on a
compressing machine equipped with punches having a
diameter equal to 16 mm and a radius of curvature equal to
20 mm.
The pressure is 21 KNewtons ~1. The hardness of
the thus obtained tablets is 35 Newtons ~5. The time of
disintegration in the mouth is from 50 to 60 seconds.

2 0 ~


EXAMPLE 4
~apidly disinteqratable multiparticulate tablet based on
coated crystals of ibuprofen.
Tablets according to the invention and whose
composition is as follows are prepared.
Formula:
ibuprofen (with 10~ of ethylcellulose) . 440 mg
reticulated polyvinylpyrrolidone . . . . 120 mg
starch commercialized under the trademark
"STARCH 1500l . . . . . . . . . . . . . 235 mg
sweetener ................................. 48 mg
aroma ~ . . . . . . . . . . . . . . . . . 52 mg
magnesium stearate . . . . . . . . . . . 5 mg
Total900 mg
This tablet is prPpared as follows.
The crystals of ibuprofen are introduced in a
fluidi~ed air bed installation and a solution of
ethylcellulose in ethanol is sprayed thereon.
The excipients are sieved and the coated ibuprofen
is homogeneized with the excipients in a mixing apparatus
under dry conditions.
Distribution and tabletting are carried out on a
compressing machine equipped with punches having a
diameter equal to 16 mm and a radius of curvature equal to
20 mm.
The pressure is 15 KNewtons +1. The hardness of
the thus obtained tablets is 50 Newtons ~5. The time of
disintegration in the mouth is from 15 to 20 seconds.
EXAMPLE 5
Rapidly di~integratable multiparticulate tablet based on
microgranules.
Formula:
microgranules with delayed release based on
doxycycline monohydrate (with 100 mg of
active principle) . . . . . . . . . . . . 225 mg

2~ 7ll


microcrystalline cellulose . . . . . . . . 142 mg
starch commercialized under the trademark
"SEPPISTAB ST 500" . . . . . . . . . . . . 98 mg
aspartam . . . . . . . . . . . . . . . . . 20 mg
aroma . . . . . . . . . . . . . . . . . . 15 mg

Total 500 mg
The microgranules are prepared in a pan by coating
a neutral sugar sphere with doxycycline according to the
classical technology, the microgranules being then coated
with Eudragit E also in coating pan.
The tablet is prepared by sieving of the
excipients, followed by homogeneization of the
microgranules of doxycycline with the excipients in a
mixing apparatus under dry conditions, followed by
distribution and tabletting in a rotary compressing
machine equipped with punches having a diameter equal to
12 mm and radius of curvature is equal to 11 mm.
The pressure is 20 KNewtons ~1. The hardness of
the thus obtained tablets is 100 Newtons +10. The time of
disintegration in the mouth is from 10 to 20 seconds.

As a result of which we have a rapidly
disintegratable multiparticulate tablet, the constitution
and method of manufacture of which are sufficiently
disclosed above, such that it would be useless to repeat
this subject and about which it is recalled that
- it consists of a tablet which combines a high level
technology (control of release, of gastroresistance, of
taste-masking of the active principle) with a high
security of use due to its multiparticulate form by way
of the coating during the process of manufacture and to
the fact that its disintegration occurs in the mouth,
- it constitutes an ambulatory form which can be adapted
to a great number of active principles and to high
dosages, which did not previously exist,

~B6~2~


- it offers a high facility of use, as the same
pharmaceutical form can be disintegrated within the
mouth, in a glass of water or in liquid or semi-liquid
food, as for example, in yoghourt for children or
infants, or in food for animals in connection with its
use in the veterinary field,
- it consists of a single and same pharmaceutical form
which can be prescribed to people requiring different
strengths; thus~ it can be used in connection with an
active principle given at its maximum dose and
manufactured in a divisible shape at one or several
scored places in such a manner that it can be
administered in totality or according to the age or the
symptoms of the patient, in the form of a divisible
part depending upon the shape of the punch, it being
emphasized that it was not obvious to obtain a
divisible multiparticulate tablet,
- it consequently consists of a pharmaceutical form which
is suitable to everybody because it offers a great
variety of means for administration and of dosages,
which represents a definite economical advantage.
The fact that a single product permits, on the one
hand, ways of administration normally permitted by several
pharmaceutical forms and that, on the other hand, it gives
rise to several posologies normally obtained by the
creation of various strengths (tablets or capsules of
different concentrations for example) cons-titutes an
economical advantage of primary importance.
In fact from the industrial point of view, this
means a single line production instead of several lines
production each corresponding to each strength selected
and to each pharmaceutical form selected.

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date 1998-05-19
(86) PCT Filing Date 1992-07-21
(87) PCT Publication Date 1993-01-23
(85) National Entry 1993-03-19
Examination Requested 1995-10-20
(45) Issued 1998-05-19
Expired 2012-07-23

Abandonment History

There is no abandonment history.

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $0.00 1993-03-19
Registration of a document - section 124 $0.00 1993-09-17
Maintenance Fee - Application - New Act 2 1994-07-21 $100.00 1994-06-17
Reinstatement: Failure to Pay Application Maintenance Fees $200.00 1995-07-31
Maintenance Fee - Application - New Act 3 1995-07-21 $100.00 1995-07-31
Maintenance Fee - Application - New Act 4 1996-07-22 $100.00 1996-06-05
Maintenance Fee - Application - New Act 5 1997-07-21 $150.00 1997-06-11
Final Fee $300.00 1998-02-10
Maintenance Fee - Patent - New Act 6 1998-07-21 $150.00 1998-05-21
Maintenance Fee - Patent - New Act 7 1999-07-21 $150.00 1999-06-21
Maintenance Fee - Patent - New Act 8 2000-07-21 $150.00 2000-06-21
Maintenance Fee - Patent - New Act 9 2001-07-23 $150.00 2001-06-26
Maintenance Fee - Patent - New Act 10 2002-07-22 $200.00 2002-06-25
Registration of a document - section 124 $100.00 2003-02-06
Registration of a document - section 124 $100.00 2003-02-06
Maintenance Fee - Patent - New Act 11 2003-07-21 $200.00 2003-06-18
Maintenance Fee - Patent - New Act 12 2004-07-21 $250.00 2004-06-25
Maintenance Fee - Patent - New Act 13 2005-07-21 $250.00 2005-06-27
Maintenance Fee - Patent - New Act 14 2006-07-21 $250.00 2006-06-27
Maintenance Fee - Patent - New Act 15 2007-07-23 $450.00 2007-06-22
Maintenance Fee - Patent - New Act 16 2008-07-21 $450.00 2008-06-26
Maintenance Fee - Patent - New Act 17 2009-07-21 $450.00 2009-06-25
Maintenance Fee - Patent - New Act 18 2010-07-21 $450.00 2010-06-25
Maintenance Fee - Patent - New Act 19 2011-07-21 $450.00 2011-06-27
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
ETHYPHARM
Past Owners on Record
BRUNA, ETIENNE
COUSIN, GERARD
GENDROT, EDOUARD
LABORATOIRES DES PRODUITS ETHIQUES ETHYPHARM
LABORATOIRES PROGRAPHARM
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
Documents

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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Claims 1997-08-06 3 139
Cover Page 1994-04-09 1 17
Abstract 1994-04-09 1 13
Claims 1994-04-09 3 106
Cover Page 1998-05-12 1 29
Description 1994-04-09 12 507
Assignment 2003-02-06 7 414
Correspondence 1998-02-10 1 36
Fees 1999-06-21 1 31
Fees 1997-06-11 1 41
Fees 1998-05-21 1 31
PCT Correspondence 1993-06-02 1 35
PCT Correspondence 1993-04-16 1 24
Office Letter 1995-12-11 1 41
Office Letter 1993-05-28 1 28
Prosecution Correspondence 1995-10-20 1 49
Prosecution Correspondence 1995-10-19 1 47
International Preliminary Examination Report 1993-03-19 23 882
Fees 1996-06-05 1 34
Fees 1995-07-31 1 47
Fees 1994-06-17 1 45