1. An apparatus for selecting a stressing voltage for compensating for changes in the threshold voltages (Vth) for drive transistors in pixel drive circuits in an active matrix OLED display having a plurality of OLED light-emitting pixels arranged in an array, comprising:
a) each pixel drive circuit being electrically connected to a data line and a power supply line, and having a drive transistor having source, drain, and gate electrodes, and a switch transistor having source, drain, and gate electrodes;
b) the source or drain electrode of each drive transistor being electrically connected to its corresponding power supply line, and the other of the source or drain electrode being electrically connected to its corresponding OLED light-emitting pixel;
c) the source or the drain electrode of each switch transistor being electrically connected to the gate electrode of its corresponding drive transistor, and the other of the source or drain electrode being electrically connected to its corresponding data line;
d) first means for applying a first voltage to the power supply lines which is either positive or negative for causing current to flow in a first direction through the drive transistors which causes the OLED light-emitting pixels to produce light in response to the signal voltages;
e) second means for applying a second voltage to the power supply lines opposite in polarity to the first voltage so that current will flow through the drive transistors in a second direction opposite to the first direction until the potential on the gate electrodes of the drive transistors causes the drive transistors to turn off;
f) third means for producing a plurality of threshold-voltage-related signals on the data lines, each of which is a function of the corresponding potentials on the gate electrodes of the drive transistors;
g) fourth means responsive to the plurality of threshold-voltage-related signals for producing a threshold-voltage-related signal; and
h) fifth means responsive to the threshold-voltage-related signal for selecting the stressing voltage.
2. The apparatus of claim 1 wherein the OLED light-emitting pixels are non-inverted OLED pixels and the first voltage is positive relative to a ground value.
3. The apparatus of claim 1 wherein the OLED light-emitting pixels are inverted OLED pixels and the first voltage is negative relative to a ground value.
4. The apparatus of claim 1 wherein the drive transistors and switch transistors are n-type transistors.
5. The apparatus of claim 1 wherein the drive transistors and switch transistors are p-type transistors.
6. The apparatus of claim 1 further including:
i) sixth means for selectively applying the stressing voltage to the gate electrodes of selected drive transistors based on the threshold-voltage-related signals to reduce the threshold voltage range in the drive transistors.
7. The apparatus of claim 6 wherein a single stressing voltage is selected to be applied or not applied based on the threshold-voltage-related signal.
8. The apparatus of claim 6 wherein one of a plurality of stressing voltages is selected to be applied based on the threshold-voltage-related signal.
9. The apparatus of claim 1 further including providing an adjustment to a signal voltage for each drive transistor wherein the adjustment from the initial threshold voltage is the same for all drive transistors.
10. The apparatus of claim 1 wherein the threshold-voltage-related signal is determined and the stressing voltage is selected for each row in the display.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A method for the preparation of citalopram comprising reacting a compound of formula (I)
30
wherein Y is a group which may be converted to cyano, with a compound having the formula
31
wherein X is a suitable leaving group and R is CH2OPg, CH2NPg1Pg2, CH2NMePg1, CON(CH3)2, CH(A1R1)(A2R2), COOR3, CH2CONH2, CHCHR7 or CONHR8, wherein Pg is a protection group for an alcohol group, Pg1 and Pg2 are protection groups for an amino group, R1 and R2 are independently selected from alkyl, alkenyl, alkynyl and optionally alkyl substituted aryl or aralkyl groups or R1 and R2 together form a chain of 2 to 4 carbon atoms, each of R3 and R7 are independently selected from alkyl, alkenyl, alkynyl and optionally alkyl substituted aryl or aralkyl, R8 is hydrogen or methyl and A1 and A2 are selected from O and S;
to form a compound of formula
32
wherein R and Y are as defined above, followed by, in either order, converting R to a dimethylaminomethyl group and converting Y to a cyano group, followed by isolating citalopram base or a pharmaceutically acceptable acid addition salt thereof.
2. The method according to claim 1 wherein the compound of formula (I) is reacted with a compound of formula (II) wherein R is CH2OPg to form a compound of formula
33
wherein Y is a group which may be converted to cyano and Pg is a protection group for an alcohol group, optionally followed by converting Y to a cyano group; followed by removing the protecting group to form a compound of formula
34
wherein Y1 is cyano or a group which may be converted to cyano, and if Y1 is not cyano, optionally followed by converting Y1 to a cyano group; and thereafter converting the alcohol group to a feasible leaving group, followed by, in either order, converting Y1 which is not cyano to cyano, and replacing the leaving group with a dimethylamino group by reacting with
a) dimethylamine or a salt thereof,
b) methylamine followed by methylation or reductive amination, or
c) with an azide followed by reduction to form the corresponding amine and thereafter methylation or reductive amination.
3. The method according to claim 1 wherein the compound of formula (I) is reacted with a compound of formula (II) wherein R is CON(CH3)2 to form a compound of the formula
35
wherein Y is as defined above, optionally followed by converting Y to a cyano group; and thereafter reducing the resulting compound to form a compound of formula
36
wherein Y1 is cyano or a compound which may be converted to cyano, and if Y1 is not cyano converting Y1 in the compound of formula (VII) to cyano.
4. The method according to claim 1 wherein the compound of formula (I) is reacted with a compound of formula (II) wherein R is CH2N(Pg1)(Pg2) to form a compound of formula
37
wherein Y is a group which may be converted to a cyano group and Pg1 and Pg2 are protection groups for an amino group, optionally followed by converting Y to a cyano group; and thereafter by removing the protecting groups to form a compound having the formula
38
wherein Y1 is a cyano group or a group which may be converted to a cyano group, followed by, in either order, converting Y1 which is not cyano to a cyano group and methylation or reductive amination of the free amino group to form citalopram.
5. The method according to claim 1 wherein a compound of formula (I) is reacted with a compound of formula (II) wherein R is CH(A1R1)(A2R2) to form a compound of the formula
39
wherein Y is a group which may be converted to a cyano group, R1 and R2 are independently selected from alkyl, alkenyl, alkynyl and optionally alkyl substituted aryl and aralkyl groups or R1 and R2 together form a chain of 2 to 4 carbon atoms and A1 and A2 are selected from O and S; optionally followed by converting Y to a cyano group; and thereafter deprotecting the compound of formula (X) to form a compound of formula
40
wherein Y1 is cyano or a group which may be converted to a cyano group and A1 is as defined above, followed by, in either order, by reductive amination with dimethylamine of the compound of formula (XI) and if Y1 is not cyano, converting Y1 to form a cyano group.
6. The method according to claim 1 wherein a compound of formula (I) is reacted with a compound of formula (II) wherein R is COOR3 where R3 is as defined above to form a compound of the formula
41
wherein Y is a group which may be converted to cyano and R3 is selected from alkyl, alkenyl, alkynyl and optionally alkyl substituted aryl and aralkyl, optionally followed by converting Y to a cyano group; and thereafter
i) reduction to form an alcohol of formula
42
wherein Y1 is cyano or a group which may be converted to cyano, and if Y1 is not cyano, optionally followed by converting Y1 to a cyano group; and thereafter converting the alcohol group to a feasible leaving group, followed by, in either order, converting Y1 which is not cyano to cyano, and replacing the leaving group with a dimethylamino group by reaction with
a) dimethylamine or a salt thereof,
b) methylamine followed by methylation or reductive amination, or
c) with an azide followed by reduction to form the corresponding amine and thereafter methylation or reductive amination, or
ii) reacting the compound of formula (XII) with an amine of NH(Me)2, NH2Me, NH3 or a salt thereof to form an amide, followed by, in either order, reducing the amide, and if Y1 is not cyano, converting the group Y1 to cyano, and if necessary methylation or reductive amination to form a dimethylamino group.
7. The method according to claim 1 wherein a compound of formula (I) is reacted with a compound of formula (II) wherein R is CH2CONH2 to form a compound of the formula
43
wherein Y is as defined above, optionally followed by converting Y to a cyano group; followed by treating the resulting compound with a hypohalide to form a compound of formula
44
wherein Y1 is a cyano group or a group which may be converted to a cyano group, followed by, in either order, converting Y1 which is not cyano to a cyano group and methylation or reductive amination of free amino group to form citalopram.
8. The method according to claim 1 wherein a compound of formula (I) is reacted with a compound of formula (II) wherein R is CHCHR7 to form a compound of the formula
45
wherein Y is a group which may be converted to a cyano group and R7 is alkyl, alkenyl, alkynyl and optionally alkyl substituted aryl and aralkyl as defined above, optionally followed by converting Y to a cyano group; and thereafter oxidizing the resulting compound to form a compound of formula
46
wherein Y1 is cyano or a group which may be converted to a cyano group, followed by, in either order, reductive amination with dimethylamine and if Y1 is not cyano, converting Y1 to a cyano group to form citalopram.
9. A method for the preparation of citalopram from a compound of formula
47
wherein Y1 is a cyano group, or a group which can be converted to a cyano group and R2 is CH2W, wherein W is a leaving group, or R2 is cyano or CH2N(CH3)2 comprising, in either order, converting Y1 which is not cyano to a cyano group and converting the group R2 which is not CH2N(CH3)2 to a dimethylaminomethyl group, followed by isolating citalopram base or a pharmaceutically acceptable acid addition salt thereof.
10. The method according to claim 9 wherein R2 is CH2W, wherein W is a leaving group and the group W is replaced by a dimethylaminomethyl group by reacting with
a) dimethylamine or a salt thereof,
b) methylamine followed by methylation or reductive amination, or
c) with an azide followed by reduction to form the corresponding amine and thereafter methylation or reductive amination.
11. The method according to claim 9 wherein group R2 is cyano which is converted to a dimethylaminomethyl group by reduction followed by methylation or reductive amination of the free base of the amino group formed.
12. The method according to claim 9 wherein the compound of formula (XVI) is prepared by reacting a compound of formula
48
wherein Y1 is a cyano group, or a group which can be converted to a cyano group, with a compound of formula
49
wherein X is a leaving group and R2 is CH2W, wherein W is a leaving group, or R2 is cyano or CH2N(CH3)2; provided that R2 is not CH2N(CH3)2 when X is halogen and Y1 is cyano; and if Y1 is not cyano, optionally followed by converting Y1 to a cyano group.
13. The method according to claim 1 wherein the compound of formula (I) is reacted with a compound of formula (II) wherein R is CH2NMe(Pg1) to form a compound of formula
50
wherein Y is a group which may be converted to a cyano group and Pg1 is a protection group for an amino group, optionally followed by converting Y to a cyano group; thereafter removing the protection group to form a compound of formula
51
wherein Y1 is a cyano group or a group which may be converted to cyano, followed by, in either order, converting Y1 which is not cyano to a cyano group and methylation or reductive amination of the amino group to form citalopram.
14. The method according to claim 1 wherein the compound of formula (I) is reacted with a compound of formula (II) wherein R is CONHR8 to form a compound of formula
52
wherein Y is a group which may be converted to cyano and wherein R8 is hydrogen or methyl, optionally followed by converting Y to a cyano group; and thereafter reducing the resulting compound to form a compound of the formula
53
wherein Y1 is cyano or a group which may be converted to cyano and R8 is hydrogen or methyl, followed by, in either order, methylation or reductive amination to form a dimethylamino group, and if Y1 is not cyano converting Y1 to a cyano group.
15. A method for the preparation of citalopram, comprising reacting a compound of formula (Ia) with a compound of formula (II) wherein R is C(A1R4)(A2R5)(A3R6) to form a compound of the formula
54
wherein Y1 is a cyano group or a group which may be converted to cyano and wherein each of R4, R5 and R6 are independently selected from alkyl, alkenyl, alkynyl and optionally alkyl substituted aryl and aralkyl and A1, A2 and A3 are selected from O and S, if Y1 is not cyano optionally followed by converting Y1 to a cyano group; and thereafter hydrolysis to form a compound of formula
55
wherein Y1 is cyano or a group which may be converted to cyano, and A1 and A2 are as defined above and if Y1 is not cyano, optionally followed by converting Y1 to cyano; and followed by
i) reducing a compound of formula (XXII) or an ester thereof to form a compound of formula
56
wherein Y1 is cyano or a group which may be converted to cyano, and if Y1 is not cyano, optionally followed by converting group Y1 to a cyano group; and thereafter converting the alcohol group to a feasible leaving group, followed by, in either order, converting Y1 which is not cyano to cyano, and replacing the leaving group with a dimethylamino group by reaction with
a) dimethylamine or a salt thereof,
b) methylamine followed by methylation or reductive amination, or
c) with an azide followed by reduction to form the corresponding amine and thereafter methylation or reductive amination, or
ii) converting the compound of formula (XXII) or an ester thereof to an amide followed by, in either order, reducing the amide, and if Y1 is not cyano, Y1 to cyano, and if necessary methylation or reductive amination to form a dimethylamino group.
16. A compound of the formula
57
wherein Y is a group which may be converted to cyano and R is CH2OPg, CH2NPg1Pg2, CH2NMePg1, CON(CH3)2, CH(A1R1)(A2R2), COOR3, CH2CONH2, CHCHR7 or CONHR8, wherein Pg is a protection group for an alcohol group, Pg1 and Pg2 are protection groups for an amino group, R1 and R2 are independently selected from alkyl, alkenyl, alkynyl and optionally alkyl substituted aryl or aralkyl groups or R1 and R2 together form a chain of 2 to 4 carbon atoms, each of R3 and R7 are independently selected from alkyl, alkenyl, alkynyl and optionally alkyl substituted aryl or aralkyl, R8 is hydrogen or methyl and A1 and A2 are selected from O and S; or an acid addition salt thereof.
17. A compound of formula
58
wherein Y1 is a group which may be converted to cyano, or an acid addition salt thereof.
18. A compound of formula
59
wherein Y1 is a compound which may be converted to cyano, or an acid addition salt thereof.
19. A compound of formula
60
wherein Y1 is a group which may be converted to a cyano group, or an acid addition salt thereof.
20. A compound of formula
61
wherein Y1 is a group which may be converted to a cyano group and A1 is O or S, or an acid addition salt thereof.
21. A compound of formula
62
wherein Y1 is a group which may be converted to a cyano group and R2 is CH2W, wherein W is a leaving group or R2 is cyano or CH2N(CH3)2, or an acid addition salt thereof.
22. A compound of formula
63
wherein Y1 is a group which may be converted to cyano, or an acid addition salt thereof.
23. A compound of formula
64
wherein Y1 is a cyano group or a group which may be converted to cyano and wherein each of R4, R5 and R6 are independently selected from alkyl, alkenyl, alkynyl and optionally alkyl substituted aryl and aralkyl and A1 , A2 and A3 are selected from O and S, or an acid addition salt thereof.
24. A compound of formula
65
wherein Y1 is cyano or a group which may be converted to cyano, and A1 and A2 is selected from O and S, or an acid addition salt thereof.