1. An optical switch comprising at least a light transmission portion, an optical path-changing portion and an actuator portion; wherein
the light transmission portion has a light reflecting plane provided on at least one part of a plane facing the optical path-changing portion to totally reflect light, and light transmission channels having optical wave guiding bodies and being provided in at least three directions with the light reflecting plane as a starting point;
the optical path-changing portion is provided in proximity to the light reflecting plane of the light transmission portion in a movable condition and has a light introduction member made of a translucent material and a light reflection member for totally reflecting light; and
the actuator portion has a mechanism that is displaced by external signals and transmits the displacement to the optical path-changing portion; and wherein
the optical path-changing portion is contacted or separated from the light reflecting plane of the light transmission portion by displacement of the actuator portion in response to the external signals; and
an optical path where light input to the light transmission channels is totally reflected at the light reflecting plane of the light transmission portion and is transmitted to a specific light transmission channel on an output side, is switched to another optical path where light input to the light transmission channel is taken to the light introduction member, and is totally reflected at the light reflection member and is transmitted to a specific light transmission channel on the output side.
2. The optical switch according to claim 1, wherein
the actuator portion has:
a piezoelectricelectrostrictive element comprising a piezoelectricelectrostrictive layer and at least one pair of electrodes arranged on one part of the piezoelectricelectrostrictive layer;
a vibrating member that is in contact with at least one part of the piezoelectricelectrostrictive element to support the piezoelectricelectrostrictive element and that converts strain of the piezoelectricelectrostrictive layer into bending displacement or vibrations;
a fixing member to fix at least one part of the vibrating member so as to vibrate the vibrating member; and
a displacement transmission member that is arranged between the optical path-changing portion and the piezoelectricelectrostrictive element based on needs, and transmits displacement of the piezoelectricelectrostrictive element to the optical path-changing portion.
3. The optical switch according to claim 2, wherein a ceramic substrate is constituted by unitarily firing the vibrating member and the fixing member, and a recessed portion or a hollow portion is formed in the ceramic substrate with giving the vibrating member a thin structure.
4. The optical switch according to claim 2, wherein the piezoelectricelectrostrictive element comprises a laminated body in which an anode layer having linking multiple layers functioning as anodes and a cathode layer having linking multiple layers functioning as cathodes are alternately laminated with a ceramic piezoelectricelectrostrictive layer being put therebetween.
5. The optical switch according to claim 1, wherein the light transmission portion comprises two or more layers having different light refractive indexes.
6. The optical switch according to claim 1, wherein the light transmission channels of the light transmission portion comprises optical waveguide.
7. The optical switch according to claim 1, wherein the light transmission portion is configured by joining at least two optical wave guiding bodies to one optical wave guiding body so as to form light transmission channels into at least three directions, with the light reflecting plane of the light transmission portion as a starting point.
8. The optical switch according to claim 1, wherein condenser lens or collimator lens is arranged at each of a plurality of light-signal input ends andor light-signal output ends of the light transmission portion, and light signals are input and output through the condenser lens or the collimator lens.
9. The optical switch according to claim 1, wherein the light reflection member is a light reflecting film that is integrally formed on a plane of the light introduction member on the side of the displacement transmission member.
10. A multichannel optical switch comprising a plurality of optical switches that has a light transmission portion, an optical path-changing portion and an actuator portion; wherein
the light transmission portion comprises: a light reflecting plane provided on at least one part of a plane facing the optical path-changing portion to totally reflect light, and light transmission channels having optical wave guiding bodies and being provided in at least three directions with the light reflecting plane as a starting point;
the optical path-changing portion is provided in proximity to the light reflecting plane of the light transmission portion in a movable condition and has a light introduction member made of a translucent material and a light reflection member for totally reflecting light; and
the actuator portion has a mechanism that is displaced by external signals and transmits the displacement to the optical path-changing portion;
and wherein the optical path-changing portion is contacted or separated from the light reflecting plane of the light transmission portion by displacement of the actuator portion in response to the external signals; and
an optical path where light input to the light transmission channels is totally reflected at the light reflecting plane of the light transmission portion and is transmitted to a specific light transmission channel on an output side, is switched to another optical path where light input to the light transmission channel is taken to the light introduction member, and is totally reflected at the light reflection member and is transmitted to a specific light transmission channel on the output side.
11. The multichannel optical switch according to claim 10, wherein each light transmission channel in a plurality of optical switches is formed of a single light transmission portion.
12. The multichannel optical switch according to claim 11, wherein each light transmission channel in a plurality of optical switches is crossed to each other and shares a part of each light transmission channel.
13. The multichannel optical switch according to claim 10, wherein one input-side channel is linked to one output-side channel in series as for each optical switch; and light that is input from an input end of optical switches, is switched at each optical path-changing portion of a plurality of optical switches.
14. The multichannel optical switch according to claim 10, wherein a plurality of optical switches are constituted by at least one optical switch having a plurality of input-side channels and at least one optical switch having a plurality of output-side channels, and one input-side channel is linked to one output-side channel between adjacent optical switches, switching the light input from input ends of a plurality of optical switches at the optical path-changing portion of the plurality of optical switches.
15. A multichannel optical switch according to claim 10, wherein a plurality of optical switches link one input-side channel to one output-side channel between adjacent optical switches by means of an optical fiber, switching at least the light input from input ends in an optical switch at each optical path-changing portion of a plurality of optical switches.
16. A multichannel optical switch in which a plurality of the multichannel switches according to claim 13 are arranged in a row.
17. A multichannel optical switch comprising a plurality of the multichannel optical switches according to claim 13; wherein each multichannel optical switch is arranged by locating at least one part of output ends themselves of each light transmission channel in each multichannel optical switch in an arc condition with an input end in an outer light transmission channel, which is disposed separately from each multichannel optical switch, at a center.
18. A multichannel optical switch in which an optical coupler is joined to a light-signal output end of each light transmission channel in the multichannel optical switches according to claim 13 to collect at least one part of the light transmission channel.
19. A multichannel optical switch in which each output end or each input end of a plurality of the multichannel optical switches according to claim 13 is linked to a plurality of input ends or output ends in at least another multichannel optical switch.
20. The multichannel optical switch according to claim 10, wherein the actuator portion comprises:
a piezoelectricelectrostrictive element having a piezoelectricelectrostrictive layer and at least one pair of electrodes arranged on one part of the piezoelectricelectrostrictive layer;
a vibrating member that is in contact with at least one part of the piezoelectricelectrostrictive element to support the piezoelectricelectrostrictive element and that converts strain of the piezoelectricelectrostrictive layer into bending displacement or vibrations;
a fixing member to fix at least one part of the vibrating member so as to vibrate the vibrating member; and
a displacement transmission member that is arranged between the optical path-changing portion and the piezoelectricelectrostrictive element based on needs and transmits displacement of the piezoelectricelectrostrictive element to the optical path-changing portion.
21. The multichannel optical switch according to claim 20, wherein a substrate of ceramics is constituted by unitarily sintering the vibrating member and the fixing member, and that a recessed portion or a hollow portion is formed in the substrate with giving the vibrating member a thin structure.
22. The multichannel optical switch according to claim 20, wherein the piezoelectricelectrostrictive element comprises a laminated body in which an anode layer of linking multiple layers as anodes and a cathode layer of linking multiple layers as cathodes are alternately laminated with a ceramic piezoelectricelectrostrictive layer being put therebetween.
23. The multichannel optical switch according to claim 10, wherein the light transmission portion is configured by joining at least two optical wave guiding bodies to one optical wave guiding body so as to form light transmission channels into at least three directions, with the light reflecting plane of the light transmission portion as a starting point.
24. The multichannel optical switch according to claim 10, wherein condenser lens or collimator lens is arranged at each of a plurality of input ends andor output ends of the light transmission portion, and light signals are input and output through the condenser lens or the collimator lens.
25. The multichannel optical switch according to claim 10, wherein the light transmission portion comprises two or more layers having different light refractive indexes.
26. The multichannel optical switch according to claim 10, wherein a light transmission channel comprising an optical wave guiding body is formed at one part of the light transmission portions.
27. The multichannel optical switch according to claim 10, wherein the light reflection member is a light reflecting film that is formed integrally on the light introduction member.
28. The multichannel optical switch according to claim 10, wherein each optical path-changing portion has a light reflection member, and at least two kinds of light reflection angles are shared among the optical path-changing portions.
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)
119
wherein:
R1 and R2 are each independently hydrogen or C1-C5 alkyl, or R1 and R2 together with the carbon atom they are commonly attached to form a C3-C6 ring;
R3 is a bond or C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl group optionally independently substituted with one to three substituent groups,
wherein each substituent group of R3 is independently C3-C8 cycloalkyl, aryl, C1-C5 alkoxy, C2-C5 alkenyloxy, C2-C5 alkynyloxy, aryloxy, acyl, C1-C5 alkoxycarbonyl, C1-C5 alkanoyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminocarbonyloxy, C1-C5 alkylaminocarbonyloxy, C1-C5 dialkylaminocarbonyloxy, C1-C5 alkanoylamino, C1-C5 alkoxycarbonylamino, C1-C5 alkylsulfonylamino, C1-C5 alkylaminosulfonyl, C1-C5 dialkylaminosulfonyl, halogen, hydroxy, carboxy, oxo, cyano, trifluoromethyl, trifluoromethoxy, nitro, or amino wherein the nitrogen atom is optionally independently mono- or di-substituted by C1-C5 alkyl or aryl; or ureido wherein either nitrogen atom is optionally independently substituted with C1-C5 alkyl; or C1-C5 alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone,
wherein each substituent group of R3 is optionally independently substituted with one to three substituent groups selected from methyl, methoxy, halogen, hydroxy, oxo, cyano, or amino;
R4 is hydrogen, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C8 cycloalkyl, heterocyclyl, aryl, heteroaryl, C1-C5 alkoxy, C2-C5 alkenyloxy, C2-C5 alkynyloxy, aryloxy, acyl, C1-C5 alkoxycarbonyl, C1-C5 alkanoyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminocarbonyloxy, C1-C5 alkylaminocarbonyloxy, C1-C5 dialkylaminocarbonyloxy, C1-C5 alkanoylamino, C1-C5 alkoxycarbonylamino, C1-C5 alkylsulfonylamino, C1-C5 alkylaminosulfonyl, C1-C5 dialkylaminosulfonyl, halogen, hydroxy, carboxy, cyano, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, nitro, or amino wherein the nitrogen atom is optionally independently mono- or di-substituted by C1-C5 alkyl; or ureido wherein either nitrogen atom is optionally independently substituted with C1-C5 alkyl; or C1-C5 alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone;
R5 and R6 are each independently hydrogen, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl group optionally independently substituted with one to three substituent groups,
wherein each substituent group of R5 and R6 are independently C3-C8 cycloalkyl, aryl, heteroaryl, C1-C5 alkoxy, C2-C5 alkenyloxy, C2-C5 alkynyloxy, aryloxy, halogen, hydroxy, oxo, cyano, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, C1-C5 alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone,
wherein each substituent group of R5 and R6 is optionally independently substituted with one to three substituent groups selected from C1-C3 alkyl, C1-C3 alkoxy, halogen, hydroxy, oxo, cyano, amino, or trifluoromethyl, or
R5 and R6 together with the carbon atom they are commonly attached to form a C3-C6 ring;
X is O, S, or amino wherein the nitrogen atom is optionally independently mono- or di-substituted by C1-C5 alkyl or aryl and the sulfur atom is optionally oxidized to a sulfoxide or sulfone;
Y is an aryl or heteroaryl group, each optionally independently substituted with one to three substituent groups,
wherein each substituent group of Y is independently C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C8 cycloalkyl, aryl, C1-C5 alkoxy, C2-C5 alkenyloxy, C2-C5 alkynyloxy, aryloxy, acyl, C1-C5 alkoxycarbonyl, C1-C5 alkanoyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminocarbonyloxy, C1-C5 alkylaminocarbonyloxy, C1-C5 dialkylaminocarbonyloxy, C1-C5 alkanoylamino, C1-C5 alkoxycarbonylamino, C1-C5 alkylsulfonylamino, C1-C5 alkylaminosulfonyl, C1-C5 dialkylaminosulfonyl, halogen, hydroxy, carboxy, cyano, trifluoromethyl, trifluoromethoxy, nitro, or amino wherein the nitrogen atom is optionally independently mono- or di-substituted by C1-C5 alkyl or aryl; or ureido wherein either nitrogen atom is optionally independently substituted with C1-C5 alkyl; or C1-C5 alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone,
wherein each substituent group of Y is optionally independently substituted with one to three substituent groups selected from methyl, methoxy, halogen, hydroxy, oxo, cyano, or amino;
n is 0, 1, 2, or 3,
or a tautomer, prodrug, solvate, or salt thereof.
2. The compound of Formula (I) according to claim 1, wherein:
R1 and R2 are each independently hydrogen or C1-C3 alkyl;
R3 is a bond or C1-C5 alkyl or C2-C5 alkenyl group optionally independently substituted with one to two substituent groups,
wherein each substituent group of R3 is independently C3-C6 cycloalkyl, phenyl, methoxy, halogen, hydroxy, oxo, cyano, trifluoromethyl, trifluoromethoxy, or C1-C5 alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone,
wherein each substituent group of R3 is optionally independently substituted with fluorine, chlorine, or bromine;
R4 is hydrogen, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C8 cycloalkyl, phenyl, furanyl, thienyl, C1-C5 alkoxy, halogen, hydroxy, cyano, trifluoromethyl, trifluoromethoxy, or C1-C5 alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone;
R5 and R6 are each independently hydrogen, C1-C5 alkyl, C2-C5 alkenyl, or C2-C5 alkynyl;
X is O, NH, or S;
Y is a phenyl group independently substituted with one to two substituent groups selected from C1-C3 alkyl, C1-C3 alkoxy, halogen, hydroxy, cyano, trifluoromethyl, or trifluoromethoxy;
n is 1,
or a tautomer, prodrug, solvate, or salt thereof.
3. The compound of Formula (I) according to claim 2, wherein:
R1 and R2 are each methyl;
R3 is a bond or C1-C5 alkyl or C2-C5 alkenyl group;
R4 is hydrogen, C3-C6 cycloalkyl, phenyl, fluorine, or chlorine;
R5 and R6 are each independently hydrogen, methyl, or ethyl;
X is O or S;
Y is a phenyl group independently substituted with one to two substituent groups selected from methoxy, fluorine, chlorine, or hydroxy,
or a tautomer, prodrug, solvate, or salt thereof.
4. The compound of Formula (I) according to claim 1, wherein:
R1 and R2 are each methyl;
R3is a bond;
R4 is a C3-C5 alkyl or C3-C5 alkenyl group;
R5 is hydrogen or methyl;
R6 is hydrogen;
X is O or S; and
Y is a 2-methoxyphenyl, 2-methoxy-5-fluorophenyl, or 2-chloro-3-hydroxyphenyl group,
or a tautomer, prodrug, solvate, or salt thereof.
5. The compound of Formula (I) according to claim 1, wherein:
R1 and R2 are each methyl;
R3 is a C2-C4 alkyl group;
R4 is phenyl group optionally monosubstituted with a fluorine or chlorine group;
R5 is hydrogen or methyl;
R6 is hydrogen;
X is O or S; and
Y is a 2-methoxyphenyl, 2-methoxy-5-fluorophenyl, or 2-chloro-3-hydroxyphenyl group,
or a tautomer, prodrug, solvate, or salt thereof.
6. The compound of Formula (I) according to claim 1, wherein:
R1 and R2 are each methyl;
R3 is a C1-C3 alkyl group;
R4 is a cyclohexyl group;
R5 is hydrogen or methyl;
R6 is hydrogen;
X is O or S; and
Y is a 2-methoxyphenyl, 2-methoxy-5-fluorophenyl, or 2-chloro-3-hydroxyphenyl group,
or a tautomer, prodrug, solvate, or salt thereof.
7. A compound selected from:
6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethylphenylamine;
(3,5-Dichlorophenyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethylamine;
4-Allylsulfanylmethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(3,5-Dichlorophenylsulfanylmethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
Allyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethylamine;
6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethylpropylamine;
4-Allyloxymethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-Benzylsulfanylmethyl-2,2-dimethyl-6-phenyl-1,2-dihydroquinoline;
4-Cyclopentylsulfanylmethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(Furan-3-ylmethylsulfanylmethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-Benzylsulfanylmethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-2,2-dimethyl-6-phenyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(2,6-dimethoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
2-6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethylsulfanyl-N-methylacetamide;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-propylsulfanylmethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-phenylsulfanylmethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
3-6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethylsulfanylpropionic acid methyl ester;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-(2-methylbutylsulfanylmethyl)-1,2-dihydroquinoline;
4-(4-tert-Butylphenylsulfanylmethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-Cyclohexylsulfanylmethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-(3-methylbutylsulfanylmethyl)-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(3-ethoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(2-ethoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
(E)-3-6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylacrylic acid ethyl ester;
4-(4-Methoxybenzylsulfanylmethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
N-6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethylbenzamide;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-(prop-2-ene-1-sulfinylmethyl)-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-(naphthalen-2-ylsulfanylmethyl)-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethylsulfanylacetic acid methyl ester;
4-(4-Chlorophenylsulfanylmethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
N-6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl-2-phenylacetamide;
6-(2-Methoxyphenyl)-4-(4-methoxyphenylsulfanylmethyl)-2,2-dimethyl-1,2-dihydroquinoline;
N-6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl-N-methylbenzamide;
4-Allylsulfanylmethyl-2,2-dimethyl-6-(2-nitrophenyl)-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-2,2-dimethyl-6-o-tolyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-dibenzofuran-4-yl-2,2-dimethyl-1,2-dihydroquinoline;
N-6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl-N-methyl-2-phenylacetamide;
4-(4-Chlorobenzylsulfanylmethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(2-fluorophenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(2-Fluorophenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-biphenyl-2-yl-2,2-dimethyl-1,2-dihydroquinoline;
6-Biphenyl-2-yl-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
Thioacetic acid S-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethylester;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-(1-phenethylsulfanylethyl)-1,2-dihydroquinoline;
4-(1-Allylsulfanylethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
2,2-Dimethyl-6-(2-methylsulfanylphenyl)-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(2,5-dimethoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(2,5-Dimethoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-(1-phenethyloxyethyl)-1,2-dihydroquinoline;
4-(1-Allyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-Benzo1,3dioxol-5-yl-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(3-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(3-Methoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(4-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(4-Methoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(3,4-dimethoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(3,4-Dimethoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-1-(3-phenylpropoxy)ethyl-1,2-dihydroquinoline;
6-(2,3-Dimethoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(2,3-dimethoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(5-Fluoro-2-methoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-2,2-dimethyl-6-(2-trifluoromethylphenyl)-1,2-dihydroquinoline;
2,2-Dimethyl-4-phenethylsulfanylmethyl-6-(2-trifluoromethylphenyl)-1,2-dihydroquinoline;
4-1-((E)-But-2-enyl)oxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-1-((E)-3-phenylallyloxy)ethyl-1,2-dihydroquinoline;
4-1-(2-Cyclohexylethoxy)ethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(1-Cyclohexylmethoxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
2-Chloro-3-(2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinolin-6-yl)phenol;
3-(4-Allylsulfanylmethyl-2,2-dimethyl-1,2-dihydroquinolin-6-yl)-2-chlorophenol;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-1-((E)-pent-2-enyl)oxyethyl-1,2-dihydroquinoline;
4-1-2-(2-Chlorophenyl)ethoxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(5-isopropyl-2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(5-Isopropyl-2-methoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-1-(3-methylbut-2-enyloxy)ethyl-1,2-dihydroquinoline;
4-(1-Allyloxyethyl)-6-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(5-Fluoro-2-methoxyphenyl)-2,2-dimethyl-4-(1-phenethyloxyethyl)-1,2-dihydroquinoline;
4-1-2-(3-Chlorophenyl)ethoxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(5-Fluoro-2-methoxyphenyl)-2,2-dimethyl-4-(1-phenethyloxyethyl)-1,2-dihydroquinoline;
4-1-2-(4-Chlorophenyl)ethoxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-1-2-(2-Bromophenyl)ethoxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-1-2-(3-Bromophenyl)ethoxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-1-(1-methylallyloxy)ethyl-1,2-dihydroquinoline;
4-(1-Allyloxypropyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(1-Allyloxybutyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(1-Allyloxy-3-phenylpropyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(1-Allyloxybut-3-enyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(1-Allyloxy-2-phenylethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(1-Allyloxy-2-methylpropyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(Allyloxyphenylmethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
Allyl-1-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylethylamine;
Allyl-1-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylethylmethylamine; and
4-(1-Allyloxyethyl)-6-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline,
or a tautomer, prodrug, solvate, or salt thereof.
8. A compound selected from:
4-Allylsulfanylmethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-Cyclopentylsulfanylmethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(Furan-3-ylmethylsulfanylmethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-propylsulfanylmethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-phenylsulfanylmethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-(2-methylbutylsulfanylmethyl)-1,2-dihydroquinoline;
4-Cyclohexylsulfanylmethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-(3-methylbutylsulfanylmethyl)-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-(1-phenethylsulfanylethyl)-1,2-dihydroquinoline;
4-(1-Allylsulfanylethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-(1-phenethyloxyethyl)-1,2-dihydroquinoline;
4-(1-Allyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-Benzo1,3dioxol-5-yl-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
6-(3-Methoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-1-(3-phenylpropoxy)ethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(5-Fluoro-2-methoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
4-1-((E)-But-2-enyl)oxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-1-((E)-3-phenylallyloxy)ethyl-1,2-dihydroquinoline;
4-1-(2-Cyclohexylethoxy)ethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(1-Cyclohexylmethoxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
2-Chloro-3-(2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinolin-6-yl)phenol;
3-(4-Allylsulfanylmethyl-2,2-dimethyl-1,2-dihydroquinolin-6-yl)-2-chlorophenol;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-1-((E)-pent-2-enyl)oxyethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-1-(3-methylbut-2-enyloxy)ethyl-1,2-dihydroquinoline;
4-(1-Allyloxyethyl)-6-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(5-Fluoro-2-methoxyphenyl)-2,2-dimethyl-4-(1-phenethyloxyethyl)-1,2-dihydroquinoline;
4-1-2-(3-Chlorophenyl)ethoxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(5-Fluoro-2-methoxyphenyl)-2,2-dimethyl-4-(1-phenethyloxyethyl)-1,2-dihydroquinoline;
4-1-2-(4-Chlorophenyl)ethoxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-1-2-(2-Bromophenyl)ethoxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-1-2-(3-Bromophenyl)ethoxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-1-(1-methylallyloxy)ethyl-1,2-dihydroquinoline;
4-(1-Allyloxypropyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(1-Allyloxy-2-methylpropyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline; and
4-(1-Allyloxyethyl)-6-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline,
or a tautomer, prodrug, solvate, or salt thereof.
9. A compound selected from:
6-(2-Methoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-(1-phenethylsulfanylethyl)-1,2-dihydroquinoline;
4-(1-Allylsulfanylethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-(1-Allyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-Allylsulfanylmethyl-6-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(5-Fluoro-2-methoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline;
4-1-((E)-But-2-enyl)oxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
2-Chloro-3-(2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinolin-6-yl)phenol;
3-(4-Allylsulfanylmethyl-2,2-dimethyl-1,2-dihydroquinolin-6-yl)-2-chlorophenol;
4-(1-Allyloxyethyl)-6-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(5-Fluoro-2-methoxyphenyl)-2,2-dimethyl-4-(1-phenethyloxyethyl)-1,2-dihydroquinoline;
6-(5-Fluoro-2-methoxyphenyl)-2,2-dimethyl-4-(1-phenethyloxyethyl)-1,2-dihydroquinoline;
4-1-2-(4-Chlorophenyl)ethoxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-1-2-(2-Bromophenyl)ethoxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
4-1-2-(3-Bromophenyl)ethoxyethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline;
6-(2-Methoxyphenyl)-2,2-dimethyl-4-1-(1-methylallyloxy)ethyl-1,2-dihydroquinoline; and
4-(1-Allyloxyethyl)-6-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline,
or a tautomer, prodrug, solvate, or salt thereof.
10. A pharmaceutical composition comprising an effective amount of a compound according to one of claims 1 to 9, or a tautomer, prodrug, solvate, or salt thereof, and a pharmaceutically acceptable excipient or carrier.
11. A method of modulating the glucocorticoid receptor function in a patient, the method comprising administering to the patient an effective amount of a pharmaceutically acceptable compound according to one of claims 1 to 9, or a tautomer, prodrug, solvate, or salt thereof.
12. A method of treating a disease-state or condition mediated by the glucocorticoid receptor function in a patient in need of such treatment, the method comprising administering to the patient an effective amount of a pharmaceutically acceptable compound according to one of claims 1 to 9, or a tautomer, prodrug, solvate, or salt thereof.
13. A method of treating a disease-state or condition selected from: type II diabetes, obesity, cardiovascular diseases, hypertension, arteriosclerosis, neurological diseases, adrenal and pituitary tumors, and glaucoma, in a patient in need of such treatment, the method comprising administering to the patient an effective amount of a pharmaceutically acceptable compound according to one of claims 1 to 9, or a tautomer, prodrug, solvate, or salt thereof.
14. A method of treating a disease characterized by inflammatory, allergic, or proliferative processes, in a patient in need of such treatment, the method comprising administering to the patient an effective amount of a pharmaceutically acceptable compound according to one of claims 1 to 9, or a tautomer, prodrug, solvate, or salt thereof.
15. The method according to claim 14, wherein the disease is selected from: (i) lung diseases; (ii) rheumatic diseasesautoimmune diseasesjoint diseases; (iii) allergic diseases; (iv) vasculitis diseases; (v) dermatological diseases; (vi) renal diseases; (vii) hepatic diseases; (viii) gastrointestinal diseases; (ix) proctological diseases; (x) eye diseases; (xi) diseases of the ear, nose, and throat (ENT) area; (xii) neurological diseases; (xiii) blood diseases; (xiv) tumor diseases; (xv) endocrine diseases; (xvi) organ and tissue transplantations and graft-versus-host diseases; (xvii) severe states of shock; (xviii) substitution therapy; and (xix) pain of inflammatory genesis.
16. The method according to claim 14, wherein the disease is selected from: type I diabetes, osteoarthritis, Guillain-Barre syndrome, restenosis following percutaneous transluminal coronary angioplasty, Alzheimer disease, acute and chronic pain, atherosclerosis, reperfusion injury, bone resorption diseases, congestive heart failure, myocardial infarction, thermal injury, multiple organ injury secondary to trauma, acute purulent meningitis, necrotizing enterocolitis, and syndromes associated with hemodialysis, leukopheresis, and granulocyte transfusion.
17. A kit for the in vitro diagnostic determination of the glucocorticoid receptor function in a sample, comprising:
(a) a diagnostically effective amount of a compound according to claim 1 or a tautomer, prodrug, solvate, or salt thereof; and
(b) instructions for use of the diagnostic kit.
18. A method of making a compound of Formula (I)
120
where R3, R4, R5, R6, X, Y, and n are as defined in claim 1 and R1 and R2 are each methyl, the method comprising: reacting the compound of Formula (VII) with a nucleophile R3R4XHm, where XHm is NH2, SH, or OH, in the presence of a suitable base to form the compound of Formula (I)
121
19. A method of making a compound of Formula (I)
122
where R3, R4, R5, R6, X, Y, and n are as defined in claim 1 and R1 and R2 are each methyl, the method comprising:
(a) reacting a 4-halonitrobenzene or 4-nitroaryltriflate of Formula (II) with an arylboronic acid of Formula (III) in the presence of a suitable palladium catalyst and base to form a biaryl compound of Formula (IV)
123
(b) reducing the nitro group of the biaryl compound of Formula (I) by reaction with a suitable reducing agent to form a compound of Formula (V)
124
(c) reacting the compound of Formula (V) with acetone in the presence of iodine to form a compound of Formula (VI)
125
(d) reacting the compound of Formula (VI) with a suitable brominating agent to form a compound of Formula (VII)
126
(e) reacting the compound of Formula (VII) with a nucleophile R3R4XHm, where XHm is NH2, SH, or OH, in the presence of a suitable base to form the compound of Formula (I)
127