1. A method of manufacturing a display panel, comprising:
forming signal lines and thin film transistors on a substrate;
forming a plurality of color filters on the signal lines and the thin film transistors;
forming a light blocking member comprising a thermochromic material on the signal lines and the thin film transistors; and
forming a plurality of pixel electrodes on the plurality of color filters and the light blocking member,
wherein the thermochromic material exhibits a black color at a temperature below a threshold temperature in a range from 78\xb0 C. to 82\xb0 C. and becomes transparent at a temperature above the threshold temperature.
2. The method of claim 1, wherein
the light blocking member further comprises a polymerizable compound and a binder.
3. The method of claim 1, wherein
a transmittance of the thermochromic material is changed within a range of 1\xb0 C. to 2\xb0 C. with reference to the threshold temperature.
4. The method of claim 1, wherein
a transmittance change with reference to the threshold temperature of the thermochromic material is reversible.
5. The method of claim 1, wherein
an optical density of the light blocking member is greater than or equal to 3.0 at the temperature below the threshold temperature, and less than or equal to 2.0 at the temperature above the threshold temperature.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
We claim:
1. A compound of formula (I) or (II):
73
wherein
R1 is selected from the group consisting of hydrogen, carboxy, C(O)C1-C6alkyl, C(O)C1-C6alkoxy, C(O)NHC1-C6alkyl-NH2, C(O)NHC1-C6alkyl-NHRA, C(O)NHC1-C6alkyl-N(RA)2, C(O)NH2, C(O)NHRA, C(O)N(RA)2, C1-C6alkyl-NH2, C1-C6alkyl-NHRA, C1-C6alkyl-N(RA)2, NHC1-C6alkyl-N(RA)2;
where each RA is independently selected from the group consisting of C1-C6alkyl, aryl, C1-C6aralkyl and heteroaryl, where the aryl, aralkyl or heteroaryl may be optionally substituted with one to three RB;
where each RB is independently selected from the group consisting of halogen, nitro, cyano, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylcarbonyl, carboxyC1-C6alkyl, C1-C6alkylsulfonyl, trifluoromethyl, amino, di(C1-C6alkyl)amino, acetylamino, carboxyC1-C6alkylcarbonylamino, hydroxyC1-C6alkylamino, NHRA and N(RA)2;
R2 is selected from the group consisting of C5-C10alkyl (optionally substituted with one to three substituents independently selected from halogen, hydroxy, nitro, amino, NHRA or N(RA)2), aryl (optionally substituted with one to three substituents independently selected from RC), cycloalkyl (optionally substituted with one to three substituents independently selected from RA), heteroaryl (optionally substituted with one to three substituents independently selected from RC), and heterocycloalkyl (optionally substituted with one to three substituents independently selected from RC);
where RC is selected from the group consisting of halogen, nitro, cyano, C1-C6alkyl, C1-C6alkoxy, trifluoromethyl, trifluoromethoxy, NH2, NH(C1-C6alkyl) and N(C1-C6alkyl)2;
R3 is selected from the group consisting of hydrogen, C1-C6alkyl, C1-C6alkylcarbonyl, C2-C6alkenylcarbonyl and C2-C6alkynylcarbonyl;
b is an integer from 0 to 4;
R4 is independently selected from the group consisting of halogen, hydroxy, carboxy, oxo, nitro, C1-C6alkyl, C1-C6alkoxy, C1-C6alkoxycarbonyl, trifluoromethyl, phenyl (wherein the phenyl group may be optionally substituted with one to three substituents independently selected from RD), phenylsulfonyl, naphthyl, C1-C6aralkyl, O-aralkyl, (wherein the aralkyl group may be optionally substituted with one to three substituents independently selected from RD), heteroaryl (wherein the heteroaryl may be optionally substituted with one to three substituents independently selected from RD), heterocycloalkyl, NH2, NHRA, N(RA)2,
74
75
where each RD is independently selected from halogen, hydroxy, carboxy, oxo, C1-C4alkyl, C1-4alkylthio, hydroxyC1-4alkyl, C1-C4alkoxy, C1-C4alkyoxycarbonyl, C1-C4alkylcarbonyl, trifluoromethyl, trifluoromethoxy, NH2, NHRA, N(RA)2, C(O)N(RA)2, SO2N(RA)2, acetylamino, nitro, cyano, formyl, C1-C6alkylsulfonyl, carboxyC1-C6alkyl and aralkyl;
c is an integer from 0 to 4;
R5 is independently selected from the group consisting of halogen, nitro, hydroxy, C1-C6alkyl, C1-C6alkoxy, NH2, NHRA, N(RA)2, ORA, C(O)NH2, C(O)NHRA, C(O)N(RA)2, NHC(O)RA, SO2NHRA, SO2N(RA)2, where RA is as defined above, phenyl (optionally substituted with one to three substituents independently selected from RB), heteroaryl (optionally substituted with one to three substituents independently selected from RB) and heterocycloalkyl (optionally substituted with one to three substituents independently selected from RB);
a is an integer from 0 to 1;
Y selected from the group consisting of C1-C6alkyl-, C(O), (C1-C6alkyl)carbonyl-, (C2-C6alkenyl)carbonyl-, (C2-C6alkynyl)carbonyl-, -carbonyl(C1-C6alkyl)-, -carbonyl(C2-C6alkenyl)-, C(O)O(C1-C6alkyl)-, C(S), SO2, (C1-C6alkyl)sulfonyl-, -sulfonyl(C1-C6alkyl)-, C(O)NH, C(O)NH(C1-C6alkyl)-, C(O)(C3-C7cycloalkyl)- and (C3-C7cycloalkyl)-C(O);
76
is selected from the group consisting phenyl, furyl, thienyl and pyrrolyl;
77
is selected from the group consisting of aryl, heteroaryl, cycloalkyl and heterocycloalkyl;
provided that when R1 is hydrogen, R3 is hydrogen, b is 0, c is 0, a is 1, Y is CH2,
78
is phenyl and
79
is phenyl, then R2 is not trimethoxyphenyl;
and pharmaceutically acceptable salts thereof.
2. The compound of claim 1 wherein
R1 is hydrogen;
R2 is selected from the group consisting of phenyl (optionally substituted with one to two substituent selected from halogen, nitro, cyano, C1-C3alkyl, C1-C3alkoxy, trifluoromethyl, trifluoromethoxy, NH2, NH(C1-C3alkyl) or N(C1-C3alkyl)2), heteroaryl and heterocycloalkyl;
R3 is selected from the group consisting of H and C1-C4alkyl;
b is an integer from 0 to 4;
R4 is selected from the group consisting of halogen, hydroxy, carboxy, oxo, C1-C3alkyl, C1-C3alkoxy, C1-C3alkoxycarbonyl, phenyl (wherein the phenyl may be optionally substituted with one to two substituents selected from hydroxy, carboxy, C1-C4alkyl, C1-4alkylthio, hydroxyC1-4alkyl, C1-C4alkoxy, C1-C4alkyoxycarbonyl, C(O)N(RA)2, trifluoromethyl, trifluoromethoxy, amino, (C1-4alkyl)amino, di(C1-4alkyl)amino, nitro, cyano or formyl), O-aralkyl, heteroaryl (wherein the heteroaryl may be optionally substituted with one to two substituents selected from hydroxy, carboxy, oxo, C1-C3alkyl, C1-C3alkoxy, C1-C3alkyoxycarbonyl, C(O)N(RA)2, trifluoromethyl, trifluoromethoxy, amino, nitro, C1-C3alkylcarbonyl or C1-4aralkyl), heterocycloalkyl,
80
c is 0;
a is an integer from 0 to 1;
Y is selected from the group consisting of C1-C4alkyl-, C(S), C(O), C(O)O(C1-C4alkyl)-, C(O)(C1-C4alkyl)-, C(O)(C2-C4alkenyl)-, C(O)(C3-C7cycloalkyl)- and C(O)NH(C1-C3alkyl)-;
81
is phenyl;
82
is selected from the group consisting of phenyl, heteroaryl and heterocycloalkyl;
and pharmaceutically acceptable salts thereof.
3. The compound of claim 2 wherein
R2 is selected from the group consisting of 3,4-methylenedioxyphenyl, 3,4-dimethoxyphenyl, 5-(2,3-dihydrobenzofuryl), 3,4-dihydrobenzo-1,4-dioxin-6-yl, 5-benzofuryl, 5-indanyl and 3-thienyl;
R3 is selected from the group consisting of H and methyl;
R4 is selected from the group consisting of bromo, hydroxy, carboxy, oxo, methyl, phenyl, 4-hydroxyphenyl, 3-hydroxymethylphenyl, 4-hydroxymethylphenyl, 4-carboxyphenyl, 4-methylphenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl, 4-methoxycarbonyl, 4-methoxycarbonylphenyl, 3-trifluoromethylphenyl, 4-cyanophenyl, 4-aminophenyl, 4-dimethylaminophenyl, 3-nitrophenyl, 4-nitrophenyl, 4-formylphenyl, 4-methylthiophenyl, benzyloxy, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, N-oxy-2-pyridinyl, 3-thienyl, 2-furyl, 1-imidazolyl, 5-(1-benzyl-2-methylimidazolyl), 5-(1,2-dimethylimidazolyl), 5-(1-methylimidazoly), 5-(1-benzylimidazolyl), 3,4-methylenedioxyphenyl,
83
Y is selected from the group consisting of CH2, C(S), C(O), C(O)OCH2, C(O)CH2CH2, C(O)CHCH, C(O)NHCH2 (107), C(O)-cyclopropyl and C(O)CH2;
84
is selected from the group consisting of phenyl, 2-furyl, 2-benzo(b)furyl, 2-pyrimidinyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1-imidazolyl, 2-imidazolyl, 2-thiazolyl, and 2-oxa-bicyclo2.2.1heptanyl;
and pharmaceutically acceptable salts thereof.
4. The compound of claim 3 wherein
R2 is selected from the group consisting of 3,4-methylenedioxyphenyl, 5-(2,3-dihydrobenzofuryl), 3,4-dihydrobenzo-1,4-dioxin-6-yl, 3-thienyl, 5-indanyl and 5-benzofuryl;
R3 is H;
b is in integer from 0 to 1;
R4 is selected from the group consisting of 5-bromo, 2-hydroxy, 6-hydroxy, 4-carboxy, phenyl, 4-hydroxyphenyl, 3-hydroxymethylphenyl, 4-hydroxymethylphenyl, 4-carboxyphenyl, 4-methylphenyl, 4-methylthiophenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl, 4-methoxycarbonyl, 4-methoxycarbonylphenyl, 3-trifluoromethylphenyl, 4-aminophenyl, 4-dimethylaminophenyl, 3-nitrophenyl, 4-nitrophenyl, 4-cyanophenyl, 4-formylphenyl, benzyloxy, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-furyl, 3-thienyl, N-oxo-2-pyridinyl, 1-imidazolyl, 5-(1-benzyl-2-methylimidazolyl), 5-1,2-dimethylimidazolyl), 3,4-methylenedioxyphenyl,
85
86
Y is selected from the group consisting of C(O), C(O)OCH2, C(O)CH2CH2, C(O)CHCH, and C(O)-cyclopropyl;
87
is selected from the group consisting of phenyl, 2-furyl, 2-benzo(b)furyl, 2-pyrimidinyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl and 2-thiazolyl;
and pharmaceutically acceptable salts thereof.
5. The compound of claim 4 wherein
R4 is selected from the group consisting of 3,4-methylenedioxyphenyl, 5-(2,3-dihydrobenzofuryl), 3,4-dihydrobenzo-1,4-dioxin-6-yl, 3-thienyl, 5-indanyl and 5-benzofuryl;
R4 is selected from the group consisting of 5-bromo, 2-hydroxy, 6-hydroxy, 4-carboxy, phenyl, 4-hydroxyphenyl, 3-hydroxymethylphenyl, 4-hydroxymethyphenyl, 4-carboxyphenyl, 4-methylphenyl, 4-methylthiophenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl, 4-methoxycarbonyl, 4-methoxycarbonylphenyl, 3-trifluoromethylphenyl, 4-aminophenyl, 4-dimethylaminophenyl, 3-nitrophenyl, 4-nitrophenyl, 4-cyanophenyl, 4-formylphenyl, benzyloxy, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, N-oxo-2-pyridinyl, 3-thienyl, 2-furyl, 1-imidazolyl, 5-(1-benzyl-2-methylimidazolyl), 5-(1,2-dimethylimidazolyl), 3,4-methylenedioxyphenyl,
88
89
Y is selected from the group consisting of C(O), C(O)OCH2 and C(O)CHCH;
and pharmaceutically acceptable salts thereof.
6. The compound of claim 5 wherein
R4 is selected from the group consisting of 6-hydroxy, 4-carboxy, phenyl, 4-hydroxyphenyl, 3-hydroxymethylphenyl, 4-methylphenyl, 4-methylthiophenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl, 4-methoxycarbonyl, 3-trifluoromethylphenyl, 3-nitrophenyl, 4-nitrophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, N-oxo-2-pyridinyl, 3-thienyl, 5-(1-benzyl-2-methylimidazolyl), 5-(1,2-dimethylimidazolyl),
90
91
and pharmaceutically acceptable salts thereof.
7. The compound of claim 6 wherein
R2 is selected from the group consisting of 3,4-methylenedioxyphenyl, and 5-(2,3-dihydrobenzofuryl);
R4 is selected from the group consisting of hydroxy, 4-methylphenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl, 4-methoxycarbonyl, 3-trifluoromethylphenyl, 4-nitrophenyl, 2-pyridinyl, 3-pyridinyl,
92
Y is selected from the group consisting of C(O) and C(O)OCH2;
93
is selected from the group consisting of 2-furyl, 2-benzo(b)furyl, 4-pyridinyl, 2-pyrimidinyl and 2-thiazolyl;
and pharmaceutically acceptable salts thereof.
8. The compound of claim 7 selected from the group consisting of 1,2,3,4-Tetrahydro-2-5-(3,4-dimethoxyphenyl)-pyrimidin-2-yl-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-3,4-bquinolin-9-one;
1,2,3,4-Tetrahydro-2-(4-pyridinyl)methyloxycarbonyl-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-3,4-bquinolin-9-one;
2,3,4-Tetrahydro-2-5-(2-pyridinyl)-pyrimidin-2-yl-3-(3,4-dihydrobenzofuranyl)-9H-pyrrolo-3,4-bquinolin-9-one;
1,2,3,4-Tetrahydro-2-5-(4-methoxyphenyl)-pyrimidin-2-yl-3-(3,4-dihydrobenzofuranyl)-9H-pyrrolo-3,4-bquinolin-9-one;
1,2,3,4-Tetrahydro-3-(3,4-methylenedioxyphenyl)-2-(5-(4-(1-(4-methyl)-piperazinylcarbonyl)-phenyl)-furoyl)-9H-pyrrolo3,4-bquinolin-9-one;
1,2,3,4-tetrahydro-2-2,3-bipyridin-6-yl-3-(2,3-dihydro-5-benzofuranyl)-9H-pyrrolo3,4-bquinolin-9-one;
2,3,4-tetrahydro-2-(2-pyridinyl)-3-(2,3-dihydro-5-benzofuranyl)-9H-pyrrolo3,4-bquinolin-9-one;
and pharmaceutically acceptable salts thereof.
9. The compound of claim 8 selected from the group consisting of
R-1,2,3,4-Tetrahydro-2-5-(3,4-dimethoxyphenyl)-pyrimidin-2-yl-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-3,4-bquinolin-9-one;
R-1,2,3,4-Tetrahydro-2-(4-pyridinyl)methyloxycarbonyl-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-3,4-bquinolin-9-one;
R-1,2,3,4-Tetrahydro-2-5-(2-pyridinyl)-pyrimidin-2-yl-3-(3,4-dihydrobenzofuranyl)-9H-pyrrolo-3,4-bquinolin-9-one;
R-1,2,3,4-Tetrahydro-2-5-(4-methoxyphenyl)-pyrimidin-2-yl-3-(3,4-dihydrobenzofuranyl)-9H-pyrrolo-3,4-bquinolin-9-one;
R-1,2,3,4-Tetrahydro-3-(3,4-methylenedioxyphenyl)-2-(5-(4-(1-(4-methyl)-piperazinylcarbonyl)-phenyl)-furoyl)-9H-pyrrolo3,4-bquinolin-9-one;
R-1,2,3,4-tetrahydro-2-(2-pyridinyl)-3-(2,3-dihydro-5-benzofuranyl)-9H-pyrrolo3,4-bquinolin-9-one;
and pharmaceutically acceptable salts thereof.
10. A compound of formula (I) or (II):
94
wherein
R1 is selected from the group consisting of hydrogen, carboxy, C(O)C1-C6alkyl, C(O)C1-C6alkoxy, C(O)NHC1-C6alkyl-NH2, C(O)NHC1-C6alkyl-NHRA, C(O)NH2, C(O)NHRA, C(O)N(RA)2, C1-C6alkyl-NH2, C1-C6alkyl-NHRA, C1-C6alkyl-N(RA)2, NHC1-C6alkyl-N(RA)2;
where each RA is independently selected from the group consisting of C1-C6alkyl, aryl, C1-C6aralkyl and heteroaryl, where the aryl, aralkyl or heteroaryl may be optionally substituted with one to three RB;
where each RB is independently selected from the group consisting of halogen, nitro, cyano, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylcarbonyl, carboxyC1-C6alkyl, C1-C6alkylsulfonyl, trifluoromethyl, amino, di(C1-C6alkyl)amino, acetylamino, carboxyC1-C6alkylcarbonylamino, hydroxyC1-C6alkylamino, NHRA and N(RA)2;
R2 is selected from the group consisting of C5-C10alkyl (optionally substituted with one to three substituents independently selected from halogen, hydroxy, nitro, amino, NHRA or N(RA)2), aryl (optionally substituted with one to three substituents independently selected from RC), cycloalkyl (optionally substituted with one to three substituents independently selected from RA), heteroaryl (optionally substituted with one to three substituents independently selected from RC), and heterocycloalkyl (optionally substituted with one to three substituents independently selected from RC);
where RC is selected from the group consisting of halogen, nitro, cyano, C1-C6alkyl, C1-C6alkoxy, trifluoromethyl, trifluoromethoxy, NH2, NH(C1-C6alkyl) and N(C1-C6alkyl)2;
R3 is selected from the group consisting of hydrogen, C1-C6alkyl, C1-C6alkylcarbonyl, C2-C6alkenylcarbonyl and C2-C6alkynylcarbonyl;
b is an integer from 0 to 4;
R4 is independently selected from the group consisting of halogen, hydroxy, carboxy, nitro, C1-C6alkyl, C1-C6alkoxy, C1-C6alkoxycarbonyl, trifluoromethyl, phenyl (wherein the phenyl group may be optionally substituted with one to three substituents independently selected from RD), phenylsulfonyl, naphthyl, C1-C6aralkyl, O-aralkyl, (wherein the aralkyl group may be optionally substituted with one to three substituents independently selected from RD), heteroaryl (wherein the heteroaryl may be optionally substituted with one to three substituents independently selected from RD), NH2, NHRA, N(RA)2,
95
where each RD is independently selected from halogen, hydroxy, carboxy, C1-C4alkyl, C1-C4alkoxy, C1-C4alkyoxycarbonyl, C1-C4alkylcarbonyl, trifluoromethyl, trifluoromethoxy, NH2, NHRA, N(RA)2, C(O)N(RA)2, SO2N(RA)2, acetylamino, nitro, cyano, formyl, C1-C6alkylsulfonyl and carboxyC1-C6alkyl;
c is an integer from 0 to 4;
R5 is independently selected from the group consisting of halogen, nitro, hydroxy, C1-C6alkyl, C1-C6alkoxy, NH2, NHRA, N(RA)2, ORA, C(O)NH2, C(O)NHRA, C(O)N(RA)2, NHC(O)RA, SO2NHRA, SO2N(RA)2, where RA is as defined above, phenyl (optionally substituted with one to three substituents independently selected from RB), heteroaryl (optionally substituted with one to three substituents independently selected from RB) and heterocycloalkyl (optionally substituted with one to three substituents independently selected from RB);
a is an integer from 0 to 1;
Y selected from the group consisting of C1-C6alkyl-, C(O), (C1-C6alkyl)carbonyl-, (C2-C6alkenyl)carbonyl-, (C2-C6alkynyl)carbonyl-, -carbonyl(C1-C6alkyl)-, -carbonyl(C2-C6alkenyl)-, C(O)O(C1-C6alkyl)-, C(S), SO2, (C1-C6alkyl)sulfonyl-, -sulfonyl(C1-C6alkyl)-, C(O)NH, C(O)NH(C1-C6alkyl)-, C(O)(C3-C7cycloalkyl)- and (C3-C7cycloalkyl)-C(O);
96
is selected from the group consisting phenyl, furyl, thienyl and pyrrolyl;
97
is selected from the group consisting of aryl, heteroaryl, cycloalkyl and heterocycloalkyl;
provided that when RA is hydrogen, R3 is hydrogen, b is 0, c is 0, a is 1, Y is CH2,
98
is phenyl and
99
is phenyl, then R2 is not trimethoxyphenyl;
and pharmaceutically acceptable salts thereof.
11. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of claim 1.
12. A pharmaceutical composition made by mixing a compound of claim 1 and a pharmaceutically acceptable carrier.
13. A process for making a pharmaceutical composition comprising mixing a compound of claim 1 and a pharmaceutically acceptable carrier.
14. A method of treating sexual dysfunction in a subject in need thereof comprising administering to the subject a therapeutically effective amount of the compound of claim 1.
15. A method of treating sexual dysfunction in a subject in need thereof comprising administering to the subject a therapeutically effective amount of the composition of claim 11.
16. The method of treating sexual dysfunction of claim 14, wherein the sexual dysfunction is male sexual dysfunction, male erectile dysfunction, impotence, female sexual dysfunction, female sexual arousal dysfunction and female sexual dysfunction related to blood flow and nitric oxide production in the tissues of the vagina and clitoris.
17. A method for increasing the concentration of cGMP in penile tissue in a male subject in need thereof comprising administering to the subject an effective amount of the compound of claim 1.
18. A method of treating a condition selected from the group consisting of male erectile dysfunction (ED), impotence, female sexual arousal dysfunction, female sexual dysfunction related to blood flow and nitric oxide production in the tissues of the vagina and clitoris, premature labor, dysmenorrhea, cardiovascular disorders, atherosclerosis, arterial occlusive disorders, thrombosis, coronary rest stenosis, angina pectoris, myocardial infarction, heart failure, ischemic heart disorders, hypertension, pulmonary hypertension, asthma, intermittent claudication and diabetic complications in a subject in need thereof comprising administering to the subject a therapeutically effective amount of the compound of claim 1.