1460937952-8dc9e616-0bca-44d2-a6b6-ec22db462cce

1. A compound of the formula:
wherein:
A and A\u2032 are each, independently, OH or OP;
P is alkyl, alkenyl, benzyl, acyl, aroyl, alkoxycarbonyl, sulfonyl or phosphoryl;
R1 and R2 are each, independently, H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, or C1\u2013C6 alkoxy;
R3 is H, halogen, or C1\u2013C6 alkyl;
R4 is H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, C3\u2013C7 cycloalkyl, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, acyl, or heteroaryl;
R5 and R6 are each, independently, H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, C3\u2013C7 cycloalkyl, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, acyl, phenyl, aryl or heteroaryl, provided that at least one of R4, R5 and R is halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, C3\u2013C7 cycloatkyl, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, acyl, phenyl, aryl or heteroaryl;
wherein the alkyl or alkenyl moieties of R4, R5 or R6 may be optionally substituted with halogen, OH, \u2014CN, trifluroalkyl, trifluoroalkoxy, \u2014NO2, or phenyl;
wherein the alkynyl moiety of R4, R5 or R6 may be optionally substituted with halogen, \u2014CN, \u2014CHO, acyl, trifluroalkyl, trialkylsilyl, or optionally substituted phenyl;
wherein the phenyl moiety of R5 or R6 may be optionally mono-, di-, or tri-subsitituted with halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, OH, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, \u2014NO2, amino, C1\u2013C6 alkylamino, di-(C1\u2013C6)alkylamino, thiol, or C1\u2013C6 alkylthio;
provided that when each of R4, R5 and R6 are H, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, or C1\u2013C6 alkoxy, then at least one of R1 and R2 is halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, or C1\u2013C6 alkoxy; provided that at least one of R4 and R6 is other than H;
or a N-oxide thereof or a pharmaceutically acceptable salt thereof or a prodrug thereof.
2. The compound of claim 1 wherein at least one of A and A\u2032 is OH.
3. The compound of claim 2 wherein A and A\u2032 are each OH.
4. The compound of claim 3 wherein R1, R2 R3 are each, independently H or halogen.
5. The compound of claim 3 wherein R5 is H, halogen, or CN.
6. The compound of claim 3 wherein R4 is H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, \u2014CN, \u2014CHO, or acyl; R6 is H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, \u2014CN, \u2014CHO, acyl, or optionally substituted phenyl; and R5 is H, halogen or \u2014CN.
7. The compound of claim 3 wherein R4 is halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, or \u2014CN; and R6 is H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, \u2014CN, or optionally substituted phenyl.
8. The compound of claim 7 wherein R5 is H, halogen or \u2014CN.
9. The compound of claim 3 wherein at least one of R1 and R2 are halogen.
10. The compound of claim 3 wherein R4 and R6 are each independently halogen, C2\u2013C7 alkynyl or CN.
11. The compound of claim 10 wherein R5 is H.
12. The compound of claim 1 wherein the compound is:
(a) 4-Chloro-2-(4-hydroxyphenyl)quinolin-6-ol,
(b) 4-Chloro-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(c) 8-Bromo-4-chloro-2-(3-fluoro-4-hydroxyphenyl)-quinolin-6-ol,
(d) 4-Bromo-2-(4-hydroxyphenyl)quinolin-6-ol,
(e) 4-Bromo-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(f) 4-Bromo-2-(3,5-difluoro-4-hydroxyphenyl)quinolin-6-ol,
(g) 4-Cyano-2-(4-hydroxyphenyl)quinolin-6-ol,
(h) 4-Cyano-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(i) 6-Acetoxy-4-bromo-2-(3-fluoro-4-acetoxyphenyl)quinoline,
(j) 2-(4-Hydroxyphenyl)-4-iodoquinolin-6-ol,
(k) 2-(3-Fluoro-4-hydroxyphenyl)-4-iodoquinolin-6-ol,
(l) 2-(3-Fluoro-4-hydroxyphenyl)-4-vinylquinolin-6-ol,
(m) 4-Ethyl-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(n) 2-(4-Hydroxyphenyl)-4-(trimethylsilyl)ethynylquinolin-6-ol,
(o) 2-(3-Fluoro-4-hydroxyphenyl)-4-(trimethylsilyl)ethynylquinolin-6-ol,
(p) 4-Ethynyl-2-(4-hydroxyphenyl)quinolin-6-ol,
(q) 4-Ethynyl-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(r) 2-(3,5-Difluoro-4-hydroxyphenyl)-4-ethynylquinolin-6-ol,
(s) 2-(3-Fluoro-4-hydroxyphenyl)-4-(phenylethynyl)quinolin-6-ol,
(t) 4-Acetyl-2-(4-hydroxyphenyl)quinolin-6-ol,
(u) 4-Acetyl-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(v) 4-(1-Hydroxyethyl)-2-(4-hydroxyphenyl)quinolin-6-ol,
(w) 2-(3-Fluoro-4-hydroxyphenyl)-4-(1-hydroxyethyl)quinolin-6-ol,
(x) 2-(3-Fluoro-4-hydroxyphenyl)-4-thiazol-2-yl-quinolin-6-ol,
(y) 2-(3-Fluoro-4-hydroxyphenyl)-4-thiophen-3-yl-quinolin-6-ol,
(z) 2-(3-Fluoro-4-hydroxyphenyl)-4-(4-pyridyl)quinolin-6-ol,
(aa) 2-(3-Fluoro-4-hydroxyphenyl)-4-(5-pyrimidyl)quinolin-6-ol,
(bb) 5-Chloro-2-(4-hydroxyphenyl)quinolin-6-ol,
(cc) 5-Bromo-2-(4-hydroxyphenyl)quinolin-6-ol,
(dd) 4-Bromo-3-chloro-2-(4-hydroxyphenyl)quinolin-6-ol,
(ee) 4-Bromo-3-chloro-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(ff) 3-Chloro-4-(4-fluorophenyl)-2-(4-hydroxyphenyl)quinolin-6-ol,
(gg) 3-Chloro-4-Cyano-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(hh) 4-Bromo-8-chloro-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(ii) 4,8-Dibromo-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(jj) 8-Chloro-4-cyano-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(kk) 8-Chloro-4-ethynyl-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(ll) 8-Chloro-2-(3-fluoro-4-hydroxyphenyl)-4-hex-1-ynylquinolin-6-ol,
(mm) 8-Chloro-2-(3-fluoro-4-hydroxyphenyl)-4-vinylquinolin-6-ol,
(nn) 8-Chloro-4-(4-cyanophenyl)-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(oo) 8-Chloro-2-(3-fluoro-4-hydroxyphenyl)-4-(4-methoxyphenyl)quinolin-6-ol,
(pp) 4-Chloro-8-cyano-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(qq) 4-Bromo-8-cyano-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(rr) 8-Cyano-4-ethynyl-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(ss) 4-Chloro-8-(4-cyanophenyl)-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol, or
(tt) 8-Cyano-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol.
13. A pharmaceutical composition comprising:
(a) a compound of the formula:
\u2003wherein:
A and A\u2032 are each, independently, OH or OP;
P is alkyl, alkenyl, benzyl, acyl, aroyl, alkoxycarbonyl, sulfonyl or phosphoryl;
R1 and R2 are each, independently, H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, or C1\u2013C6 alkoxy;
R3 is H, halogen, or C1\u2013C6 alkyl;
R4 is H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, C3\u2013C7 cycloalkyl, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, acyl, or heteroaryl;
R5 and R6 are each, independently, H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, C3\u2013C7 cycloalkyl, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, acyl, phenyl, aryl or heteroaryl, provided that at least one of R4, R5 and R6 is halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, C3\u2013C7 cycloalkyl, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, acyl, phenyl, aryl or heteroaryl;
wherein the alkyl or alkenyl moieties of R4, R5 or R6 may be optionally substituted with halogen, OH, \u2014CN, trifluroalkyl, trifluoroalkoxy, \u2014NO2, or phenyl;
wherein the alkynyl moiety of R4, R5 or R6 may be optionally substituted with halogen, \u2014CN, \u2014CHO, acyl, trifluroalkyl, trialkylsilyl, or optionally substituted phenyl;
wherein the phenyl moiety of R5 or R6 may be optionally mono-, di-, or tri-subsitituted with halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, OH, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, \u2014NO2, amino, C1\u2013C6 alkylamino, di-(C1\u2013C6)alkylamino, thiol, or C1\u2013C6 alkylthio;
provided that when each of R4, R5 and R6 are H, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, or C1\u2013C6 alkoxy, then at least one of R1 and R2 is halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, or C1\u2013C6 alkoxy;
provided that when R4 is H, then R3 is halogen or C1\u2013C6 alkyl;

or a N-oxide thereof or a pharmaceutically acceptable salt thereof or a prodrug thereof; and
(b) a pharmaceutical carrier.
14. A compound of the formula:
wherein:
A and A\u2032 are each, independently, OH or OP;
P is alkyl, alkenyl, benzyl, acyl, aroyl, alkoxycarbonyl, sulfonyl or phosphoryl;
R1 and R2 are each H;
R3 is H, halogen, or C1\u2013C6 alkyl;
R4, R5 and R6 are each, independently, H, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, or C1\u2013C6 alkoxy, provided that at least one of R4, R5 and R6 is C1\u2013C6 alkyl, C2\u2013C7 alkenyl, or C1\u2013C6 alkoxy;

wherein the alkyl or alkenyl moieties of R4, R5 or R6 may be optionally substituted with halogen, OH, \u2014CN, trifluroalkyl, trifluoroalkoxy, \u2014NO2, or phenyl;
or a N-oxide thereof or a pharmaceutically acceptable salt thereof or a prodrug thereof; and
(b) a pharmaceutical carrier.
17. A compound of formula
wherein:
A and A\u2032 are each, independently, OH or OP;
P is alkyl, alkenyl, benzyl, acyl, aroyl, alkoxycarbonyl, sulfonyl or phosphoryl;
R1 and R2 are each, independently, H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, or C1\u2013C6 alkoxy;
R3 is H;
R4 is H, aryl, or substituted aryl;
R5 and R6 are each, independently, H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, C3\u2013C7 cycloalkyl, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, acyl, phenyl, aryl or heteroaryl, provided that at least one of R5 and R6 is halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, C3\u2013C7 cycloalkyl, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, acyl, phenyl, aryl or heteroaryl;
wherein the alkyl or alkenyl moieties of R5 or R6 may be optionally substituted with halogen, OH, \u2014CN, trifluroalkyl, trifluoroalkoxy, \u2014NO2, or phenyl;
wherein the alkynyl moiety of R5 or R6 may be optionally substituted with halogen, \u2014CN, \u2014CHO, acyl, trifluroalkyl, trialkylsilyl, or optionally substituted phenyl;
wherein the phenyl moiety of R5 or R6 may be optionally mono-, di-, or tri-subsitituted with halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, OH, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, \u2014NO2, amino, C1\u2013C6 alkylamino, di-(C1\u2013C6)alkylamino, thiol, or C1\u2013C6 alkylthio;

or a N-oxide thereof or a pharmaceutically acceptable salt thereof or a prodrug thereof.
18. The compound of claim 17 wherein said compound is:
(a) 2-(3-Fluoro-4-hydroxyphenyl)-4-phenylquinolin-6-ol,
(b) 2-(3-Fluoro-4-hydroxyphenyl)-4-(methylphenyl)quinolin-6-ol,
(c) 2-(3-Fluoro-4-hydroxyphenyl)-4-(4-fluorophenyl)quinolin-6-ol,
(d) 4-(4-Chlorophenyl)-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol,
(e) 4-(4-Cyanophenyl)-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol, or
(f) 2-(3-Fluoro-4-hydroxyphenyl)-4-(4-trifluoromethylphenyl)quinolin-6-ol.
19. A pharmaceutical composition comprising:
(a) a compound of formula
\u2003wherein:
A and A\u2032 are each, independently, OH or OP;
P is alkyl, alkenyl, benzyl, acyl, aroyl, alkoxycarbonyl, sulfonyl or phosphoryl;
R1 and R2 are each, independently, H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, or C1\u2013C6 alkoxy;
R3 is H;
R4 is H, aryl, or substituted aryl;
R5 and R6 are each, independently, H, halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, C3\u2013C7 cycloalkyl, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, acyl, phenyl, aryl or heteroaryl, provided that at least one of R5 and R6 is halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, C2\u2013C7 alkynyl, C3\u2013C7 cycloalkyl, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, acyl, phenyl, aryl or heteroaryl;
wherein the alkyl or alkenyl moieties of R5 or R6 may be optionally substituted with halogen, OH, \u2014CN, trifluroalkyl, trifluoroalkoxy, \u2014NO2, or phenyl;
wherein the alkynyl moiety of R5 or R6 may be optionally substituted with halogen, \u2014CN, \u2014CHO, acyl, trifluroalkyl, trialkylsilyl, or optionally substituted phenyl;
wherein the phenyl moiety of R4, R5 or R6 may be optionally mono-, di-, or tri-subsitituted with halogen, C1\u2013C6 alkyl, C2\u2013C7 alkenyl, OH, C1\u2013C6 alkoxy, \u2014CN, \u2014CHO, \u2014NO2, amino, C1\u2013C6 alkylamino, di-(C1\u2013C6)alkylamino, thiol, or C1\u2013C6 alkylthio;

or a N-oxide thereof or a pharmaceutically acceptable salt thereof or a prodrug thereof; and
(b) a pharmaceutical carrier.

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 nonvolatile semiconductor memory device comprising:
a memory cell array including memory cells arranged at intersections of a plurality of word lines and a plurality of bit lines intersecting each other, each of the memory cells comprising an antifuse element comprising a MOS transistor, the MOS transistor including a first terminal, a second terminal, and a gate electrode formed on a gate insulating film, and a select transistor connected between the second terminal and one of the bit lines, and being selectively turned on;
a row decoder configured to receive a writing instruction signal and a reading instruction signal to selectively activate one of the word lines according to an input state of a row address signal;
a data buffer configured to receive a data input signal and drive corresponding one of the bit lines when the writing instruction signal is received, and amplify a minute reading signal transmitted to one of the bit lines to output a data output signal when the reading instruction signal is received; and
a power supply circuit configured to supply a certain voltage to the first terminal of the memory cell,
wherein the data buffer drives the corresponding one of the bit lines to a first voltage while the power supply circuit supplies a second voltage higher than the first voltage to the first terminal when the writing instruction signal is received,
whereas the data buffer drives the corresponding one of the bit lines to a third voltage while the power supply circuit supplies a fourth voltage lower than the third voltage to the first terminal when the reading instruction signal is received.
2. The nonvolatile semiconductor memory device according to claim 1, wherein the power supply circuit includes a charge pump circuit configured to boost a power supply voltage up to a certain boosted voltage in response to the writing instruction signal thereby supplying the boosted voltage to an output terminal.
3. The nonvolatile semiconductor memory device according to claim 1, wherein
the power supply circuit comprises
an output terminal operative to output an certain boosted voltage, the boosted voltage being generated by boosting a power supply voltage, and
a ground potential clamping circuit configured to clamp the output terminal to a ground potential, and
the ground potential clamping circuit is turned on in response to the reading instruction signal.
4. The nonvolatile semiconductor memory device according to claim 3, wherein the power supply circuit includes a charge pump circuit configured to boost a power supply voltage up to a certain boosted voltage in response to the writing instruction signal thereby supplying the boosted voltage to an output terminal.
5. The nonvolatile semiconductor memory device according to claim 1, wherein
the power supply circuit comprises
an output terminal operative to output an certain boosted voltage, the boosted voltage being generated by boosting a power supply voltage, and
a ground potential clamping circuit configured to clamp the output terminal to a ground potential.
6. The nonvolatile semiconductor memory device according to claim 5, wherein the power supply circuit includes a charge pump circuit configured to boost a power supply voltage up to a certain boosted voltage in response to the writing instruction signal thereby supplying the boosted voltage to an output terminal.
7. The nonvolatile semiconductor memory device according to claim 1, wherein
the power supply circuit comprises
an output terminal operative to output an certain boosted voltage, the boosted voltage being generated by boosting a power supply voltage, and
a ground potential clamping circuit configured to clamp the output terminal to a ground potential, and
the ground potential clamping circuit is turned on in response to the reading instruction signal.
8. The nonvolatile semiconductor memory device according to claim 7, wherein the power supply circuit includes a charge pump circuit configured to boost a power supply voltage up to a certain boosted voltage in response to the writing instruction signal thereby supplying the boosted voltage to an output terminal.
9. The nonvolatile semiconductor memory device according to claim 1, wherein
a transistor configuring the memory cell is an n type enhancement type MOS transistor.
10. The nonvolatile semiconductor memory device according to claim 1, wherein
a transistor configuring the memory cell is an n type depression type MOS transistor.
11. A nonvolatile semiconductor memory device comprising:
a memory cell array including memory cells arranged at intersections of a plurality of word lines and a plurality of bit lines intersecting each other, each of the memory cells comprising an antifuse element comprising a MOS transistor, the MOS transistor including a first terminal, a second terminal, and a gate electrode formed on a gate insulating film, and a select transistor connected between the second terminal and one of the bit lines, and being selectively turned on;
a row decoder configured to receive a writing instruction signal and a reading instruction signal to selectively activate one of the word lines according to an input state of a row address signal;
a data buffer configured to receive a data input signal when the writing instruction signal is received, and drive corresponding one of the bit lines and amplify a minute reading signal transmitted to one of the bit lines to output a data output signal when the reading instruction signal is received;
a plurality of plate lines commonly coupled to the memory cells arranged along a first direction;
a plate line drive circuit configured to selectively drive the plate lines according to an output signal of the row decoder; and
a power supply circuit configured to supply a boosted voltage,
the plate line drive circuit being operative to supply a certain boosted voltage to the plate lines while the data buffer drives the corresponding one of the bit lines to a first voltage lower than the boosted voltage according to the writing instruction signal, the boosted voltage being generated by the power supply circuit,
whereas
the plate line drive circuit being operative to supply a second voltage lower than the boosted voltage to the plate lines while the data buffer drives the corresponding one of the bit lines to a third voltage higher than the second voltage according to the read instruction signal.
12. The nonvolatile semiconductor memory device according to claim 11,
wherein a transistor configuring the memory cell is p type MOS transistor.
13. The nonvolatile semiconductor memory device according to claim 11, wherein the power supply circuit includes a charge pump circuit configured to boost a power supply voltage up to a certain boosted voltage in response to the writing instruction signal thereby supplying the boosted voltage to an output terminal.
14. The nonvolatile semiconductor memory device according to claim 11, wherein
the power supply circuit comprises
an output terminal operative to output an certain boosted voltage, the boosted voltage being generated by boosting a power supply voltage, and
a ground potential clamping circuit configured to clamp the output terminal to a ground potential, and
the ground potential clamping circuit is turned on in response to the reading instruction signal.
15. The nonvolatile semiconductor memory device according to claim 14, wherein the power supply circuit includes a charge pump circuit configured to boost a power supply voltage up to a certain boosted voltage in response to the writing instruction signal thereby supplying the boosted voltage to an output terminal.
16. The nonvolatile semiconductor memory device according to claim 11, wherein
the power supply circuit comprises
an output terminal operative to output an certain boosted voltage, the boosted voltage being generated by boosting a power supply voltage, and
a ground potential clamping circuit configured to clamp the output terminal to a ground potential.