What is claimed is:
1. A semiconductor device having a flip chip structure, the semiconductor device comprising:
a chip;
a chip mounting member;
a plurality of function bumps provided on said chip for electrically connecting said chip to said chip mounting member; and
a supporting member interposed between said chip and said chip mounting member, wherein said supporting member acts against a local bending force of said chip.
2. The semiconductor device according to claim 1, wherein said supporting member is disposed at a point-symmetric vacant position of said function bumps with respect to a point of a center of said chip.
3. The semiconductor device according to claim 1, wherein said point-symmetric vacant position is limited to a predetermined corner region of said chip.
4. The semiconductor device according to claim 3, wherein a size of said corner region is (D3)(E3), where D and E are lengths of the sides of said semiconductor device.
5. The semiconductor device according to claim 1, wherein said supporting member is disposed at a portion of a predetermined bump position set on said chip closest to each corner.
6. The semiconductor device according to claim 1, wherein said supporting member are dummy bumps provided on said chip, wherein said dummy bumps are not electrically connected to said chip mounting member.
7. The semiconductor device according to claim 6, wherein a region of a surface of said chip mounting member with which said dummy bumps come into contact is coated with an electrically insulating protective film.
8. The semiconductor device according to claim 1, wherein said supporting member are metal wires projecting from said chip into a projecting direction of said function bumps in a form of a loop.
9. The semiconductor device according to claim 1, wherein said supporting member are resilient projections projecting from one of said chip and said chip mounting member toward the other one.
10. The semiconductor device according to claim 1, wherein said supporting member are a set of resilient projections respectively projecting from said chip and said chip mounting member toward the other ones.
11. The semiconductor device according to claim 1, wherein said supporting member are resilient spacers independent from both said chip and chip mounting member.
12. The semiconductor device according to claim 11, wherein an underfill resin is charged into a gap between said chip and said chip mounting member.
13. The semiconductor device according to claim 1, wherein said supporting member are resilient fillers, an underfill resin is charged into a gap between said chip and said chip mounting member to bury said filler into said underfill resin.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
What is claimed is:
1. A method of preparing an arylretinamide comprising:
a) reacting hexachloroacetone with a solvent-suspended resin-bound triphenylphosphine to provide a suspension comprising an activated chlorinating reagent;
b) reacting retinoic acid with the activated chlorinating reagent to provide retinoyl chloride;
c) adding pyridine and a select arylamine to the reaction mixture and stirring the resulting mixture for a time and at a temperature sufficient for the arylamine to react with the retinoyl chloride and provide the arylretinamide.
2. The method of claim 1 further comprising the step of purifiying the arylretinamide from the suspension.
3. The method of claim 2 wherein purification is accomplished by treatment of the reaction mixture with solid phase reagents to remove unreacted starting materials followed by chromatography.
4. The method of claim 1 wherein step (a) is performed at a temperature ranging from about 0 C. to room temperature.
5. An arylretinamide for inducing apoptosis in a cancer cell, said arylretinamide having Structure A, B, or C below:
10
wherein
R2 is H, OH, NO2, CH2 OH, a halide, or an alkyl comprising 1-4 carbon atoms, R3 is H, OH, NO2, CO2CH3, CO2CH2CH3, CO2(CH2)2CH3, CO2(CH2)3CH3, CO2H, CH2OH, a halide, or an alkyl comprising 1-4 carbon atoms;
R4 is H, OH, OCH3, OCH2CH3, O(CH2)2CH3, O(CH2)3CH3, SO2CH3, SO2CH2CH3, SO2(CH2)2CH3, SO2(CH2)3CH3, NH2, NHCOCH3, NHCOCH2CH3, NHCO(CH2)2CH3, NHCO(CH2)3CH3, NHCOCF3, N3, NCS, a halide, an alkyl comprising 1-4 carbon atoms, or NHCOCH2X, wherein X is a halide;
R5 is H, NO2, C(CH3)3, C(CH2CH3)3, C((CH2)2CH3)3, C((CH2)3CH3)3, CO2CH3, CO2CH2CH3, CO2(CH2)2CH3, CO2(CH2)3CH3, a halide, or an alkyl comprising 1-4 carbon atoms, and
R6 is H, CO2H, CO2CH3, CO2CH2CH3, CO2(CH2)2CH3, CO2(CH2)3CH3, a halide or an alkyl comprising 1-4 carbon atoms; provided however that when R2, R3, R4, R5, and R6 are all H, R4 is not OH or OCH2CH3; and also provided that when R3, R5, and R6 are all H, and R2 is OH, R4 is not CO2CH3.
11
wherein the OH group is at position 2,4, or 5 when the retinamido group is at linked to position 1, and the OH group is at position 3 when the rentinamido group is linked to position 2.
12
wherein R7 is C1 to C4 alkyl.
6. The arylretinamide of claim 5 wherein the arylretinamide is a halohydroxyphenyl retinamides which comprises a phenyl moiety that is optionally substituted with an alkyl group.
7. The arylrentiamide of claim 6 wherein the phenyl moiety is substituted with a methyl group.
8. The arylreninamide of claim 6 wherein the halo group is an iodo group.
9. The arylretinamide of claim 5 wherein the arylretinamide is a hydroxy-alkylphenyl retinamides or hydroxy-alkoxyphenyl retinamide, wherein the alkyl groups attached to the phenyl moiety comprise from 1 to 4 carbon atoms.
10. The arylretinamide of claim 9 wherein the arylretinamide is a hydroxy-methylphenyl or hydroxy-methoxyphenyl retinamide.
11. The arylretinamide of claim 5 is a hydroxy-nitrophenyl retinamides or alkylsulfonyl-hydroxy retinamides.
12. The arylretinamide of claim 11 wherein the arylretinamide is an ethylsulfonyl-hydroxy, retinamides.
13. The arylretinamide of claim 5 wherein the arylretinamide is a hydroxy-napthylphenyl retinamide.
14. The arylretinamide of claim 5 wherein the arylretinamide is an N-alkyl(hydroxyphenyl) retinamides.
15. The arylretinamide of claim 5 wherein the arylretinamide is an aminophenyl retinamides.
16. The arylretinamide of claim 5 wherein the arylretinamdie is an alkylhydroxyphenyl retinamides.
17. The arylretinamide of claim 5 wherein the arylretinamide is a carboxy-hydroxyphenyl retinamides selected from the group consisting of N-(2-hydroxy-3-carboxymethylphenyl)retinamide, N-(2-hydroxy-3-carboxyphenyl)retinamide, N-(2-hydroxy-6-carboxymethyphenyl)retinamide, N-(2-hydroxy-6-carboxyphenyl)retinamide, N-(3-hydroxy-4-carboxymethylphenyl)retinamide, N-(3-hydroxy-4-carboxyphenyl)retinamide, N-(2-hydroxy-5-carboxymethylphenyl)retinamide, N-(2-hydroxy-4-carboxyphenyl)retinamide, N-(4-hydroxy-3-carboxymethylphenyl)retinamide, and N-(4-hydroxy-3-carboxyphenyl)retinamide.
18. An arylretinamide having Structure A below
13
wherein
R2 is H, OH, NO2, CH2 OH, a halide, or an alkyl comprising 1-4 carbon atoms,
R3 is H, OH, NO2, CO2CH3, CO2CH2CH3, CO2(CH2)2CH3, CO2(CH2)3CH3, CO2H, CH2OH, a halide, or an alkyl comprising 1-4 carbon atoms; R4 is H, OH, OCH3, OCH2CH3, O(CH2)2CH3, O(CH2)3CH3, SO2CH3, SO2CH2CH3, SO2(CH2)2CH3, SO2(CH2)3CH3, NH2, NHCOCH3, NHCOCH2CH3, NHCO(CH2)2CH3, NHCO(CH2)3CH3, NHCOCF3, N3, NCS, a halide, an alkyl comprising 1-4 carbon atoms, or NHCOCH2X, wherein X is a halide;
R5 is H, NO2, C(CH3)3, C(CH2CH3)3, C((CH2)2CH3)3, C((CH2)3CH3)3, CO2CH3, CO2CH2CH3, CO2(CH2)2CH3, CO2(CH2)3CH3, a halide, or an alkyl comprising 1-4 carbon atoms, and
R6 is H, CO2H, CO2CH3, CO2CH2CH3, CO2(CH2)2CH3, CO2(CH2)3CH3, a halide, or an alkyl comprising 1-4 carbon atoms;
provided that when R2, R3, R4, R5, and R6 are all H, R4 is not OH OCH3, OCH2CH3, or O(CH2)2CH3; and also
provided that when R3, R5, and R6 are all H, and R2 is OH, R4 is not CO2CH3 or CO2CH2CH3.
19. A method of inducing apoptosis in a cancer cell comprising contacting the cancer cell with an arylretinamide of claim 1.
20. A method of treating cancer in a subject in need of said treatment, comprising administering one or more arylretinamides of claim 1 to the subject.
21. The method of claim 20 wherein said method further comprises administering calcium glucarate to the subject.