Title of Invention

PRINTED CARD BASED USER INTERFACE SYSTEM

Abstract An user interface for reading data recorded in infrared on the face of a card upon which may also be recorded a visual representation is disclosed. The data may include text and/or images equivalent to recording a book, newspaper, manual or a database. Figure 1
Full Text

PRINTED CARD BASED USER INTERFACE SYSTEM
FIELD OF THE INVENTION
. The present invention relates to an user interface system for recovering digital data
printed in infrared ink in a fault tolerant encoded form on a print media using an inkjet printing system. In particular, tlie data may be encoded on the same surface as a human readable representation, for example an image which is related to the data which is encoded thereon.

The disclosures of these co-pending applications are incorporated herein by reference.
Various methods, systems and apparatus relating to the present invention are disclosed in the following co-pending appHcatíon filed by the applicant or assignee of the present invention on July 10,1998:
USSN 09/113,070
USSN 09/112,785 The disclosures of this co-pending application are incorporated herein by reference.
Various methods, systems and apparatus relating to the present invention are disclosed in the following co-pending applications filed by the applicant or assignee of the present

invention on June 30,2000:
PCT/AU00/00743, PCT/AUOO/OO744, PCT/AU00/00745, PCT/AU00/00746,
PCT/AU00/00747 and PCT/AU00/00748 The disclosures of these co-pending applications are incorporated herein by reference.
BACKGROUND OF THE INVENTION
The applicant has disclosed in pending applications USSN 09/113,070 and USSN
09/112,785 cards called Artcards in which the information is encoded in black ink on a white background on the reverse face of the printed card, the front surface of the card bearing an image. The data that may be recorded may be the contents of a book recorded in a digital manner with the from face bearing an image equivalent to the dust jacket of the book.
In such prior art, two printheads are required in order to simultaneously print the image on the front of the card and the digital data on the rear of the card. To read the card, the card is passed through an optical scanning means and the fault tolerant encoded data is reconstructed and decoded and provided to a user as an audio or visual output.
SUMMARY OF THE INVENTION
The present invention provides a user interface for reading data encoded •in a fault
tolerant form in infrared ink on a surface simultaneously bearing an image.
It is an object of the present invention to provide an apparatus for reading data encoded in a fault tolerant digital form printed in invisible ink on a surface of a card said surface bearing an image comprising:
a) scanning means for scanning said encoded fault tolerant digital form of said data on said surface in the infrared;
b) means for processing said scanned data and for decoding said data into 'a secondary digital format;
c) means for outputting said data in said secondary digital format to an output device with which said secondary digital format is usable;
d) said output device presenting said data in a human readable form.
Preferably the invisible ink may be an infrared (IR) absorbing ink with negligible absorption in the visible spectrum.
Preferably, the data is encoded on the card using a Reed-Solomon encoding process after compression of the data. This allows recovery of the data notwithstanding up to 30%

damage to the print media upon which the data is recorded (image encoded form). The card for example may be a standard card as disclosed in co-pending applications lodged hereto PCT/AU01/01317 (Docket No. ART8O), PCT/AU01/01328 (Docket No. ART8l) and PCT/AU01/01326 (Docket No. ART82) of the size of a photograph of approximately 4" x 6" (102mm x 152mm). It is also contemplated that other formats are also possible for the card for example of the same width but shorter or longer depending upon the amount of data which is recorded or to be recorded on the print media.
BRIEF DESCRIPTION OF THE DRAWINGS
Notwithstanding any other form which may fall within the scale of the present
invention, preferred forms of the invention will now be described by way of example only with reference to the accompanying drawing of Fig 1 which illustrates the card reading arrangement of the preferred embodiment.
DESCRIPTION OF THE PREFERRED AND OTHER EMBODIMENTS
The preferred embodiment is preferably implemented through sµitable
programming of a hand held device such as that described in the applicant's applications PCT/AU01/01317 (Docket No. ART8O), PCT/AU01/01328 (Docket No. ART8l) and PCT/AU01/01326 (Docket No. ART82) filed concurrently herewith by the present applicant the content of which is hereby specifically incorporated by reference. These applications make reference to tl:ie applicant's prior applications USSN 09/113,070 and USSN 09/112,785.
The aforementioned patent specifications disclose an apparatus including a camera system, hereinafter known as an "Artcam" type camera system, wherein sensed images can be directly printed out by the camera unit using an Inkjet pagewidth printhead having at least four separate Inkjet nozzles for printing a color image and an infi:ared image simultaneously on a print media. A pagevvddth printhead of this type was described by the applicant in co-pending applications PCT/AU00/00743, PCT/AU00/00744, PCT/AU00/00745, PCT/AU0O/00746, PCT/AU00/00747 and PCT/AU00/00748 and the descriptions thereof are hereby specifically incorporated by reference.
In the above referenced patent specifications, namely PCT/AU01/01317, (Docket No. ART8O), PCT/AU01/01328 (Docket No. ART8l) and PCT/AU01/01326 (Docket No. ART82), data in a fault tolerant encoded form is printed in infi¾red ink over a color image. The data which was described in each of these

specifications related respectively to storing a fault tolerant encoded digital form of the image itself, a fault tolerant encoded digital form of the image itself along with an image processing program script which enabled the image to be processed to produce a given effect thereon, and a copy of the image itself and of a transformed copy of that image, the transformation being achieved by a program which could be separately loaded into the camera system.
In the present application, the invention resides in recording digital data on an image, the digital data relating to other than the image itself or any manipulation thereof. For example, as described in the applicant's prior art of USSN 09/113,070 a card may be printed using a fault tolerant digitally encoded form comprising a book on one surface of a print media while on the other face of the print media an image is recorded, for example in this case the dust jacket of the book. The cards that were described were of the size of a credit card of approximately 85mm x 55mm size. The card was printed on both faces. In the present invention the card needs only to be printed on one face with the data being recorded in infra red ink and thus invisible to a human reader. As described in the applicant's co-pending applications PCT/AU01/01317 (Docket No. ART8O), PCT/AU01/01328 (Docket No. ART8l) and PCT/AU01/01326 (Docket No. ART82), a card of approximate size 4" x 6" (102mm x 152mm) can contain approximately 3-
4megabytes of data depending on how the data is encoded and distributed across the surface of the card. The data in those applications is distributed in such a way that full recovery of the data there encoded, namely an image, can be recovered even if up to 30% damage has occurred to the surface of the card. To store an average page of text requires approximately 2 kbytes of digital data for text only, hence 3 megabytes of data would record approximately 1.5 thousand pages of written text. An average book contains between 250-550 pages and such a book is readily accommodated by the format of the present disclosure. In addition, :images may be interspersed with the text as thumbnail (reduced sized) images in a suitable file format for example jpeg, gif, tiff, bmp to name a few.
The preferred embodiment provides an adaptation of the particular technology as disclosed in the aforementioned patent specifications PCT/AU01/01317 (Docket No. ART8O), PCT/AU01/01328 (Docket No. ART8l) and PCT/AU01/01326 (Docket No. ART82). In this adaptation, the camera system and the printing system is

dispensed with and replaced with a large screen reader. The cards according to the preferred embodiment are then provided having an indicator of the information which is recorded on the card. The information in a fault tolerant encoded form is printed in infrared ink over that indicator. For example the card could include a book's content or a newspaper content. An example of such a system is as illustrated in Fig 1 wherein the card 10 includes a book title on the card with data printed thereon in infrared ink as shown by arrow 11. The card 10 is inserted in the reader 12 which includes a flexible display 13 which allows for the folding up of the card reader 12. The card reader includes display controls 14 which allow for paging forward and back and other controls of the card reader 12.
It can therefore be seen that the arrangement of Fig 1 provides for an efficient distribution of information in the form of books, newspapers, magazines, technical manuals, and so forth.
Various inkjet technologies can be used for printing of the card according to the cxirrent disclosure, for example íin inkjet pagewidth printhead such as disclosed in the applicant's co-pending applications PCT/AU00/00743, PCT/AU00/00744, PCT/AU00/00745, PCT/AU00/00746, PCT/AU00/00747 and PCT/AU00/00748 may be used. Suitable infrared ink is disclosed in the applicant's co-pending applications, Australian provisional patent applications PQ94I2 and PQ9376 filed on 14 August 2000 and applicant's applications PQ95O9 filed on 18 August 2000, and PQ957l, and PQ956l filed on 21 August 2000. Data may be encoded in a manner or using a format as disclosed in applicant's USSN 09/113,070 and USSN 09/112,785, or PCT/AU01/01317 (Docket No. ART8O), PCT/AU01/01328 (Docket No. ART8l) and PCT/AU01/01326 (Docket No. ART82), for example the Artcard format or the alternative Artcard format. Other formats may be used.
It would be appreciated by a person skilled in the art that numerous vari^atio¤s and/or modifications may be made to the present invention as shown in the specific embodiment without departing from the spirit or scope of the invention as broadly described. The present invention is, therefore, to be considered in all respects to be illustrative and not restrictive.




CLAIMS:
1. An apparatus for reading data encoded in a fault tolerant digital form printed in
invisible ink on a surface of a card said surface bearing an image, said data at least including
a fault tolerant digital form of said image, said apparatus comprising:
a) scanning means for scanning in said encoded fault tolerant digital form of said data on said surface;
b) means for processing said scanned data and for decoding said data in to a secondary digital format;
c) means for outputting said secondary digital format to an output device with which said secondary digital format is useable;
d) said output device presenting said data in a human readable form.

2. An apparatus as claimed in claim 1 wherein said data is encoded in a fault tolerant digital form using a Reed-Solomon process and said means for processing and decoding said data includes means for processing saidRccd-Solomon process.
3. An apparatus as claimed in claim 2 wherein said output device includes a display device,
4. An apparatus as claimed in claim 1 wherein said invisible ink is an infrared absorbing ink with negligible absorption in the visible spectrum.

4, An apparatus for reading data encoded in a fault tolerant digital form substantially as herein described with reference to the accompanying
drawing.




Field of the invention
The present invention relates to a process for the preparation of biologically active piperidylmethyl-indanones derivative. The present invention more particularly relates to an improved process for the preparation of benzyl-piperidylmethyl-indanones derivative of formula (I).

Description of the prior art
Biologically important compound of benzyl-piperidylmethyl-indanones derivative is 1 -benzyl-4- [(5,6-dimethoxy-1 -indanon)-2-yl]methylpiperidine generically known, as Donepezil. Donepezil is useful as a medicament, specifically as an acetyl cholinesterase inhibitor, more specifically as an agent for preventing, treating and improving various kinds of senile dementia, cerebrovascular dementia or attention deficit hyperactivity disorder (ADHD), and further specifically as an agent for preventing, treating and improving Alzheimer-type senile dementia. Donepezil is a new drug treatment for use in mild to moderate dementia due to SDAT. Donepezil acts by inhibiting acetylcholine esterase, the enzyme responsible for metabolising acetylcholine, thereby enhancing neurotransmitter levels.
JP-A 64-79151(1989) discloses a process for the preparation of Donepezil by reacting 5,6-dimethoxy-l-indanone with 1-benzyl-4-formylpiperidine in the presence of strong base such as lithium diisopropylamide followed by reduction.
JP-A 8-225527 (1996) (EP-711,756-A1, U.S. Pat. No. 5,606,064) discloses a process for the preparation of Donepezil, which comprises reaction of 5,6-dimethoxy-l-indanone with pyridin-4-aldehyde afforded 5,6-dimethoxy-2-(pyridin-4-yl)methyleneindan-l-one followed by reaction with benzyl bromide

afforded 1 -benzyl-4-(5,6-dimethoxyindan-1 -on-2-ylidene)methylpiridinium
bromide, then reduction in the presence of platinum oxide afforded Donepezil. The reduction in the last step was not reproducible. Hence suffers in scaleup.
W097/22584 describes a process which involves reaction of (pyridin-4-yl)
carboxyaldehyde with malonic acid afforded 3-(pyridin-4-yl) -2-propenoic acid,
followed by reduction afforded 3- (piperidin-4-yl) -2-propionic acid, followed by
reaction with methyl chlorocarbonate afforded 3-[N- (methoxycarbonyl) piperidin-
4-yl] propionic acid, followed by reaction with oxalyl chloride afforded methyl 4-
(2-chlorocarbonylethyl)piperidin-l-carboxylate, followed by reaction with 1,2-
dimethoxybenzene in the presence of aluminum chloride afforded methyl 4-[3-
(3,4-dimethoxyphenyl)-3-oxopropyl]piperidin-l-carboxylate, followed by reaction
with tetramethyldiaminomethane afforded methyl 4-[2-(3,4-
dimethoxybenzoyl)allyl]piperidin-l-carboxylate, followed by treatment with sulfuric acid afforded methyl 4-(5,6-dimethoxy-l-oxoindan-2-ylmethyl) piperidin-1-carboxylate, followed by treatment with base afforded 5,6-dimethoxy-2-(piperidin-4-ylmethyl)indan-l-one , then reaction with benzyl bromide afforded Donepezil. This patent involves more steps as a consequence suffers in yield. US pat No. 5,606,064 discloses a process for the preparation of benzyl-piperidylmethy-indanones. The said process involves the following scheme-1:

Scheme-l
US pat. No 5,100,901 discloses a process whish is described in Scheme-2


In view of the biological importance of Donepezil and to have a commercially viable, easily scalable process which do not use hazards reagents, we focused our research to found an improved process for the preparation of the compound of formula (I), which process has advantages over the processes described in the above-mentioned prior art documents.
Objectives of the invention
The main objective of the present invention is to provide an improved process for the preparation of compound of general formula (I).
Another objective of the present invention is to give a process for the preparation of compound of formula (I), which avoids use of hazardous chemicals and would be easy to implement on commercial scales.
Still another objective of the present invention is to provide a process for the preparation of compounds of formula (I) in good yield and high purity.
Summary of the invention:
Accordingly, the present invention provides an improved process for the preparation of compounds of formula (I)

the said process comprising the steps of:

(i) reacting the compound of formula (II) wherein X represents chloro, bromo, iodo, fluoro with the compound of formula (III) in the absence or presence of base in the absence or presence of a solvent at a temperature in the range of -10°C to the reflux temperature, to produce compound of formula (IV), (ii) reacting the compound of formula (IV) with the compound of formula (V) wherein X represents chloro, bromo, iodo, fluoro in the absence or presence of a solvent at a temperature in the range of -20°C to the reflux temperature, to produce the pyridinium salt of formula (VI),
(iii) hydrogenating pyridinium salt of formula (VI) to compound of formula (VII) in the absence or presence of a solvent at a temperature in the range of-20°C to the reflux temperature, and
(iv) oxidising the compound of formula (VII) using an oxidising agent in the absence or presence of a solvent at a temperature in the range of -20°C to the reflux temperature, to produce the compound of formula (I). The process is shown in scheme-3 below:


Detailed description of the invention
In an embodiment of the present invention the reaction compound of formula (II) with the compound of formula (III) can be carried out either Wittig type reaction, Grignard type reaction.
In another embodiment of the present invention the Wittig reaction can be carried out by the reaction of compound of formula (II) with triphenyl phosphine and then by reacting resulting compound with compound of formula (III).
In still another embodiment of the present invention the Grignard reaction can be carried out by the reaction of compound of formula (II) with magnesium and then by reacting resulting compound with compound of formula (III).
In another embodiment of the present invention the solvent employed in step (i) is selected from esters, ethers, alkanols, nitrile, ketones, hydrocarbon, halogenated hydrocarbon, DMF, DMAc, diglyme, monoglyme, THF, dioxane, sulpholane and the like or mixtures thereof.
In another embodiment of the present invention the base employed in step (i) is selected from butyl lithium, LDA, alkali/alkali earth metal hydroxide, alkali/alkali earth metal carbonates, alkali/alkali earth metal bicarbonates, alkali/alkali earth metal oxides, alkali/alkali earth tert butoxide, alkoxide, metal amides, metal hydrides and the like.
In yet another embodiment of the present invention the solvent employed in step (ii) is selected from ethers, esters, halogenated hydrocarbon, hydrocarbons, THF and the like or mixtures thereof.
In yet another embodiment of the present invention the hydrogenation in step (iii) is carried out using platinum and also platinum compounds, palladium, palladium on carbon, Raney nickel, ruthenium and also ruthenium compounds, if appropriate on support materials such as active carbon or silica.
In yet another embodiment of the present invention the solvent employed in hydrogenation in step (iii) is carried out using ethers, such as diethyl ether, dibutyl

ether, methyl tert-butyl ether, dioxane or tetrahydrofuran, alcohols such as methanol, ethanol, propanol, isopropanol or butanol, chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or dichloroethylene, acetone, acetonitrile, dimethylformamide, dimethyl sulphoxide, N-methylpyrrolidone or tetramethylurea; hydrocarbons such as hexane, toluene, benzene or xylene, water, acetic acid , formic acid, TFA and the like or mixtures thereof.
In still another embodiment of the present invention the oxidisng agent employed in step (iv) is selected from KMn04, Cr03/H2S04, ruthenium tetroxide, CH3COOOH, H2O2, Br2, Mn02, Pb(0Ac)4/pyridine, NaOCl/AcOH, Se02, N2O3, pyridinium chlorochromate, DDQ, CAN, benzeneselenic anhydride, NaBrOs/CAN, Na2Cr207 and the like and the solvent employed is selected from ethers, alkanols, esters, nitrile, halogenated hydrocarbon, DMF, DMAc, diglyme, monoglyme, THF, dioxane and the like or mixtures thereof.
In yet another embodiment of the present invention the compound of formula (I) prepared to the process of present invention is useful in the preparation of Donepezil HCl.

Documents:

0553-chenp-2003 abstract.jpg

0553-chenp-2003 claims duplicate.pdf

0553-chenp-2003 description (provisional).pdf

0553-chenp-2003 description(complete) duplicate.pdf

0553-chenp-2003 drawings duplicate.pdf

553-chenp-2003 claims granted.pdf

553-chenp-2003 form 18.pdf

553-chenp-2003 form 3.pdf

553-chenp-2003 petition.pdf

553-chenp-2003 power of attorney.pdf

553-chenp-2003-abstract.pdf

553-chenp-2003-claims.pdf

553-chenp-2003-correspondnece-others.pdf

553-chenp-2003-correspondnece-po.pdf

553-chenp-2003-description(complete).pdf

553-chenp-2003-drawings.pdf

553-chenp-2003-form 1.pdf

553-chenp-2003-form 18.pdf

553-chenp-2003-form 3.pdf

553-chenp-2003-form 5.pdf

553-chenp-2003-pct.pdf


Patent Number 228913
Indian Patent Application Number 553/CHENP/2003
PG Journal Number 12/2009
Publication Date 20-Mar-2009
Grant Date 11-Feb-2009
Date of Filing 17-Apr-2003
Name of Patentee SILVERBROOK RESEARCH PTY LTD
Applicant Address 393 DARLING STREET, BALMAIN, NEW SOUTH WALES 2041,
Inventors:
# Inventor's Name Inventor's Address
1 SILVERBROOK, KIA SILVERBROOK RESEARCH PTY LTD, 393 DARLING STREET, BALMIN, NEW SOUTH WALES 2041,
2 LAPSTUN, PAUL SILVERBROOK RESEARCH PTY LTD, 393 DARLING STREET, BALMIN, NEW SOUTH WALES 2041,
3 WALMSLEY, SIMON, ROBERT SILVERBROOK RESEARCH PTY LTD, 393 DARLING STREET, BALMIN, NEW SOUTH WALES 2041,
PCT International Classification Number G06K 7/12
PCT International Application Number PCT/AU01/01325
PCT International Filing date 2001-10-19
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 09/693,226 2000-10-20 U.S.A.