1. A process for preparing a compound of formula B:
which process comprises converting a compound of formula VII:
to the compound of formula B, wherein R1, R2 and R3 are the same or different and signify hydrogens, halogens, alkyl, alkyloxy, hydroxy, nitro, alkylcarbonylamino, alkylamino or dialkylamino group; R4 is alkyl or aryl; and R5 is \u2014N3 or \u2014NH2, wherein: the term alkyl means hydrocarbon chains, straight or branched, containing from one to six carbon atoms, optionally substituted by aryl, alkoxy, halogen, alkoxycarbonyl or hydroxycarbonyl groups; the term aryl means a phenyl or naphthyl group, optionally substituted by alkyloxy, halogen or nitro group; and the term halogen means fluorine, chlorine, bromine or iodine.
2. The process according to claim 1, wherein at least one of R1, R2 and R3 is fluorine.
3. The process according to claim 1, wherein R4 is C1 to C4 alkyl, preferably R4 is methyl, ethyl or t-butyl, more preferably R4 is methyl.
4-5. (canceled)
6. The process according to claim 1, wherein R4 is benzyl.
7. The process according to any preceding claim 1, wherein compound VII has the formula I:
8. The process according to claim 1, wherein compound VII has the formula IA:
9. The process according to claim 1, wherein compound VII has the formula V:
10. The process according to claim 1, wherein compound VII has the formula VA:
11. (canceled)
12. The process according to claim 7, wherein the conversion comprises a Hoffman rearrangement.
13. The process according to claim 9, wherein the conversion comprises a Curtius rearrangement.
14. The process according to claim 12, wherein the conversion comprises effecting a rearrangement of the amide group to the carbamate group in the presence of a hypohalite and an alcohol of the formula R4OH, wherein R4 is alkyl or aryl, preferably R4 is C1 to C4 alkyl, preferably R4 is methyl, ethyl or t-butyl, more preferably R4 is methyl or benzyl.
15-17. (canceled)
18. The process according to claim 1, wherein the compound of formula B is purified by recrystallisation.
19. (canceled)
20. The process according to claim 7, wherein the compound of formula I is prepared by converting a compound of formula II:
to the compound of I, wherein R1, R2 and R3 have the same meaning as in compound I.
21-25. (canceled)
26. The process according to claim 1, wherein the compound of formula B has the following formula:
and the process for preparing the compound of formula B comprises the following steps:
27. The process according to claim 13, wherein conversion of V to B comprises thermal decomposition in the presence of an alcohol having the formula R4OH, wherein R4 is C1 to C4 alkyl, preferably R4 is methyl, ethyl or t-butyl, more preferably R4 is methyl or benzyl.
28-37. (canceled)
38. The process according to claim 27, wherein the compound of formula V is prepared by converting a compound of formula VI:
to the compound of V, wherein R1, R2, and R3 have the same meanings as for compound V.
39-47. (canceled)
48. The process according to claim 38, wherein the compound of formula VI is prepared by converting a compound of formula II:
to the compound of formula VI, wherein R1, R2, and R3 have the same meanings as compound VI.
49-53. (canceled)
54. The process according to claim 20, wherein the compound of formula II is prepared by converting a compound of the formula III:
to the compound of formula II, wherein R1, R2 and R3 have the same meanings as in compound II.
55-63. (canceled)
64. The process according to claim 54, wherein the compound of formula III is prepared by converting a compound of formula IV:
to the compound of formula III, wherein R1, R2 and R3 have the same meanings as in compound III.
65-81. (canceled)
82. The process according to claim 64, wherein the compound of formula B has the following formula:
and the process for preparing the compound of formula B comprises the following steps:
83. The process according to claim 64, wherein the compound of formula B has the following formula:
and the process for preparing the compound of formula B comprises the following steps:
84. The process according to claim 1, wherein the compound of formula B is converted to the S or R enantiomer of a compound of formula A,
wherein R1, R2, R3 are the same or different and signify hydrogens, halogens, alkyl, alkyloxy, hydroxy, nitro, alkylcarbonylamino, alkylamino or dialkylamino group, preferably at least one of R1, R2 and R3 is fluorine and wherein R4 is alkyl or aryl, preferably R4 is C1 to C4 alkyl, preferably R4 is methyl, ethyl or t-butyl, more preferably R4 is methyl or benzyl.
85-91. (canceled)
92. The process according to claim 84, wherein the process further comprises converting the R or S enantiomer of compound A to the respective R or S enantiomer of a compound of formula C, or a salt thereof,
wherein R1, R2 and R3 are the same or different and signify hydrogens, halogens, alkyl, alkyloxy, hydroxy, nitro, alkylcarbonylamino, alkylamino or dialkylamino group, wherein: the term alkyl means hydrocarbon chains, straight or branched, containing from one to six carbon atoms, optionally substituted by aryl, alkoxy, halogen, alkoxycarbonyl or hydroxycarbonyl groups; and the term halogen means fluorine, chlorine, bromine or iodine.
93. The process according to claim 92, wherein the R or S enantiomer of the compound of formula C, or a salt thereof, is converted to the respective R or S enantiomer of a compound of formula E or a salt thereof,
wherein R12 signifies hydrogen, alkyl or alkylaryl group; and n is 1, 2 or 3.
94. The process according to claim 93, wherein the R or S enantiomer of the compound of formula C is reacted with a compound of formula D2:
to produce the respective R or S enantiomer of a compound of formula E or a salt thereof,
wherein n signifies 1, 2 or 3; R12 signifies hydrogen, alkyl or alkylaryl group, R11 signifies a hydroxyl protecting group and R13 signifies an amino protecting group, or R11 is defined as above but R12 and R13 taken together represent a phthalimido group; with a water soluble thiocyanate salt in the presence of an organic acid in a substantially inert solvent, followed by subsequent deprotection of the intermediate products F to I:
95-96. (canceled)
97. The process according to claim 94, wherein the compound of formula E is (R)-5-(2-aminoethyl)-1-chroman-3-yl-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(6-hydroxychroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(8-hydroxychroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(6-methoxychroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(8-methoxychroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(6-fluorochroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(8-fluoro chroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(6,7-difluorochroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(6,8-difluorochroman-3-yl-1,3-dihydroimidazole-2-thione; (S)-5-(2-aminoethyl)-1-(6,8-difluorochroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(6,7,8-trifluoro chroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(6-chloro-8-methoxychroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(6-methoxy-8-chlorochroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(6-nitrochroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(8-nitrochroman-3-yl)-1,3-dihydro imidazole-2-thione; (R)-5-(2-aminoethyl)-1-6-(acetylamino)chroman-3-yl-1,3-dihydroimidazole-2-thione; (R)-5-aminomethyl-1-chroman-3-yl-1,3-dihydroimidazole-2-thione; (R)-5-aminomethyl-1-(6-hydroxychroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-aminoethyl)-1-(6-hydroxy-7-benzylchroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-aminomethyl-1-(6,8-difluorochroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(3-aminopropyl)-1-(6,8-difluorochroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-benzylaminoethyl)-1-(6-methoxychroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-5-(2-benzylaminoethyl)-1-(6-hydroxychroman-3-yl)-1,3-dihydroimidazole-2-thione; (R)-1-(6-hydroxychroman-3-yl)-5-(2-methylaminoethyl)-1,3-dihydroimidazole-2-thione; (R)-1-(6,8-difluorochroman-3-yl)-5-(2-methylaminoethyl)-1,3-dihydroimidazole-2-thione or (R)-1-chroman-3-yl-5-(2-methylaminoethyl)-1,3-dihydroimidazole-2-thione or a salt thereof.
98. (canceled)
99. The process according to claim 97, wherein the salt is the hydrochloride salt.
100. The process according to claim 94, wherein the compound of formula E is the R or S enantiomer of the compound of formula P.
101. A compound of formula I:
wherein R1, R2 and R3 are the same or different and signify hydrogens, halogens, alkyl, alkyloxy, hydroxy, nitro, alkylcarbonylamino, alkylamino or dialkylamino group, wherein: the term alkyl means hydrocarbon chains, straight or branched, containing from one to six carbon atoms, optionally substituted by aryl, alkoxy, halogen, alkoxycarbonyl or hydroxycarbonyl groups; the term aryl means a phenyl or naphthyl group, optionally substituted by alkyloxy, halogen or nitro group; and the term halogen means fluorine, chlorine, bromine or iodine.
102. (canceled)
103. A compound of formula V:
104. (canceled)
105. A compound of formula VI:
106. (canceled)
107. A compound of formula II:
108-109. (canceled)
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 voice coil motor, comprising:
a movable receiving cylinder having an inner receiving space for receiving a lens module, the receiving cylinder comprising a first end and an opposite second end, the first end adjacent to an object side of the lens module and the second end adjacent to an image side of the lens module; the receiving cylinder comprising a plurality of protrusions formed at the first end;
a wire coil fixed to the receiving cylinder and surrounding the receiving cylinder;
a hollow fixing frame receiving the receiving cylinder and the wire coil;
a group of magnetic members fixed to an inner wall of the fixing frame and surrounding the wire coil, the magnetic members and the wire coil cooperatively configured for generating a magnetic driving force for driving the receiving cylinder to move in the fixing frame;
a top elastic member comprising a peripheral portion and a central portion resiliently connected to the peripheral portion, the central portion having a central opening and a plurality of cutouts formed in an inner edge thereof in the central opening, the protrusions of the receiving cylinder engaged in the cutouts, the peripheral portion being fixed at a position lower than the central portion, thereby forming an elastic force applied to the receiving cylinder in a direction from the first end to the second end when no current is applied to the wire coil; and
a bottom elastic member connected to the receiving cylinder and the fixing frame, the bottom elastic member being in an undeformed state when no current is applied to the wire coil.
2. The voice coil motor of claim 1, wherein the receiving cylinder further comprises a rim, a plurality of ribs are formed at an outer wall of the rim of the receiving cylinder, the rim extending outwards from the outer wall along a circumferential direction of the receiving cylinder, the ribs extending upwards from the rim along a central axis direction of the receiving cylinder, the wire coil fixed on the rim, the ribs configured for creating a first space between the wire coil and the outer wall of the receiving cylinder.
3. The voice coil motor of claim 2, wherein the fixing frame comprises a base, a frame and a cover, the frame has a top panel having an opening, and a plurality of tabs depending from an inner wall of the top panel in the opening along a central axis direction of the frame, a second space is formed between the inner wall of the frame and each of the tabs, each of the tabs extending into the first space, and the magnetic members being received in the respective second space.
4. The voice coil motor of claim 1, further comprising a ring-shaped clamping member for clamping the peripheral portion of top elastic member, a height of each of the magnetic members is less than a height of the receiving cylinder, the clamping member clamping the peripheral portion of the top elastic member on the magnetic members.
5. The voice coil motor of claim 1, wherein the top elastic member has a plurality of slots formed between the peripheral portion and the central portion.
6. The voice coil motor of claim 1, wherein the receiving cylinder has an inner thread formed in the inner wall of the inner space threadedly engaging with the lens module.
7. An image capturing module, comprising:
a voice coil motor of claim 1; and
a lens module received in the inner space of the receiving cylinder of the voice coil motor.