(IN-306827) Aryl alkyl ethers and method thereof 机翻标题: 暂无翻译,请尝试点击翻译按钮。

源语言标题
(IN-306827) Aryl alkyl ethers and method thereof
公开号/公开日
IN306827IN2406/DEL/2015 / 2019-02-052017-02-10
申请号/申请日
IN2406/DEL/2015 / 2015-08-05
发明人
RANGARAJAN Thakku MohanBRAHMA RajuSINGH RajendraSINGH Rishi PalSINGH Raj Pal;
申请人
DEFENCE RESEARCH & DEVELOPMENT ORGANISATION;
主分类号
IPC分类号
B01F
摘要
(IN306827) The present invention relates to a compound of Formula I or its stereoisomers, prodrugs and pharmaceutically acceptable salts thereof. The present disclosure further relates to a process of preparing an aryl alkyl ether compound, comprising: reacting an aryl halide or triflate or mesylate or tosylate with an alcohol in the presence of a base, a catalyst, and a ligand to obtain an aryl alkyl ether compound.
机翻摘要
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地址
代理人
代理机构
;
优先权号
2015IN-DE02406
主权利要求
(IN306827) 1. A compound of Formula I or its stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein: Z is selected from the group of or, wherein A is selected from the group consisting of heteroaryl, aryl, alkyl, cycloalkyl, and heterocyclyl, wherein heteroaryl, aryl, alkyl, cycloalkyl, heterocyclyl can be optionally substituted with 1 to 9 substituents independently selected from R1, wherein R1 is selected from the group of electron withdrawing group, electron donating group, and substituted derivatives thereof; R2 is alkyl, wherein alkyl is unsubstituted or independently substituted with up to seventeen substituents independently selected from alkyl, alkenyl, alkynyl, alkoxy, acyl, acyloxy, acylamino, amino, monoalkylamino, dialkylamino, trialklamino, deuteriu m, -O(CH2)1-10OCH3, halogen, hydroxy, hydroxyalkyl, keto, thiocarbonyl, carboxy, alkylcarboxy, hydroxyami no, alkoxyamino, nitro, azido, cyano, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, hetero cyclyl, heterocyclylalyl, heteroaryl and heteroarylalkyl, cycloalkenyl, cycloalkylamino, arylamino, heterocyclylamino, heteroarylamino, cycloalkyloxy, aryloxy, heterocyclylox y, heteroaryloxy, ethyl acetohydroximate or substituted derivatives thereof, wherein alkoxy, -O(CH2)1-10OCH3 is unsubstituted or independently substituted with up to seven substituents independently selected from deuterium, and halogen; x is 0-9; y is 1 to 5, wherein a compound of Formula I or its stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, is selected from the group consisting of: (E)-3-(4-(2-fluoroethoxy)phenyl)-1-phenylprop-2-en-1-one (1) (E)-3-(4-(2-fluoroethoxy)phenyl)-1-(p-tolyl)prop-2-en-1-one (2) (E)-3-(4-(2-fluoroethoxy)phenyl)-1-(4-fluorophenyl)prop-2-en-1-one (3) (E)-1-(4-(2-fluoroethoxy)phenyl)-3-(3-nitrophenyl)prop-2-en-1-one (4) (E)-3-(4-(benzyloxy)phenyl)-1-(4-(2-fluoroethoxy)phenyl)prop-2-en-1-one (5) (E)-1-(4-(2-fluoroethoxy)phenyl)-3-(p-tolyl)prop-2-en-1-one (6) (E)-3-(3,4-dimethoxyphenyl)-1-(4-(2-fluoroethoxy)phenyl)prop-2-en-1-one (7) (E)-1-(4-(2-fluoroethoxy)phenyl)-3-(4-fluorophenyl)prop-2-en-1-one (8) (E)-3-(4-(2-fluoroethoxy)phenyl)-1-(naphthalen-1-yl)prop-2-en-1-one (9) (E)-1-(4-(2-fluoroethoxy)phenyl)-3-(3,4,5-trimethox-yphenyl)prop-2-en-1-one (10) (E)-3-(4-(2-fluoroethoxy)phenyl)-1-(2-methoxyphenyl)prop-2-en-1-one (11) (E)-1-(4-(2-fluoroethoxy)phenyl)-3-(5-(2-fluoroethoxy)thiophen-2-yl)prop-2-en-1-one (12) (E)-1,3-bis(4-(2-fluoroethoxy)phenyl)prop-2-en-1-one (13) (E)-1-(p-tolyl)-3-(4-(2,2,2-trifluoroethoxy)phenyl)prop-2-en-1-one (14) (E)-3-(p-tolyl)-1-(4-(2,2,2-trifluoroethoxy)phe nyl)prop-2-en-1-one (15) (E)-3-(4-(benzyloxy)phenyl)-1-(4-(2,2,2-trifluoro-ethoxy)phenyl)prop-2-en-1-one (16) (E)-1-(4-(2,2,2-trifluoroethoxy)phenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (17) (E)-1,3-bis(4-(2,2,2-trifluoroethoxy)-phenyl)prop-2-en-1-one (18) (E)-3-(2,5-dimethoxyphenyl)-1-(4-(2,2,2-trifluoroethoxy)phenyl)prop-2-en-1-one (19) (E)-3-(4-fluorophenyl)-1-(4-(2,2,2-trifluoroethoxy)phenyl)prop-2-en-1-one (20) (E)-3-(3-nitrophenyl)-1-(4-(2,2,2-trifluoro-ethoxy)phenyl)prop-2-en-1-one (21) (E)-1-(2-methoxyphenyl)-3-(4-(2,2,2-trifluoro-ethoxy)phenyl)prop-2-en-1-one (22) (E)-1-(4-fluorophenyl)-3-(4-(2,2,2-trifluoroethoxy)-phenyl)prop-2-en-1-one (23) (E)-1-(naphthalen-1-yl)-3-(4-(2,2,2-trifluoroethoxy)-phenyl)prop-2-en-1-one (24) (E)-3-(4-(2,2,3,3,3-pentafluoropropoxy)phenyl)-1-phenylprop-2-en-1-one (25) (E)-3-(4-(2,2,3,3,3-pentafluoropropoxy)phenyl)-1-(p-tolyl)prop-2-en-1-one (26) (E)-1-(4-(2,2,3,3,3-pentafluoropropoxy)phenyl)-3-(p-tolyl)prop-2-en-1-one (27) (E)-3-(4-(2,2,3,3,4,4,4-heptafluorobutoxy)phenyl)-1-(p-tolyl)prop-2-en-1-one (28) (E)-3-(2,5-dimethoxyphenyl)-1-(4-(2,2,3,3,4,4,4-heptafluorobutoxy)phenyl)prop-2-en- 1-one (29) (E)-3-(4-(benzyloxy)phenyl)-1-(4-(2,2,3,3,4,4,4-heptafluorobutoxy)phenyl)prop-2-en-1- one (30) (E)-1-(4-methoxyphenyl)-3-(3-(2,2,2-trifluoroethoxy)phenyl)prop-2-en-1-one (31) (E)-1-phenyl-3-(4-(2,2,2-trifluoroethoxy)phenyl)prop-2-en-1-one (32) (E)-3-(3-(2-fluoroethoxy)phenyl)-1-phenylprop-2-en-1-one (33) (E)-3-(3-(2-fluoroethoxy)phenyl)-1-(4-methylphenyl)prop-2-en-1-one (34) (E)-3-(3-(2-fluoroethoxy)phenyl)-1-(4-methoxyphenyl)prop-2-en-1-one (35) (E)-1-(3-(2-fluoroethoxy)phenyl)-3-(4-methylphenyl)prop-2-en-1-one (36) (E)-3-(3,4-dimethoxyphenyl)-1-(3-(2-fluoroethoxy)phenyl)prop-2-en-1-one (37) (E)-1-(3-(2-fluoroethoxy)phenyl)-3-(3-methoxyphenyl)prop-2-en-1-one (38) (E)-3-(2-(2-fluoroethoxy)phenyl)-1-(4- methoxyphenyl)prop-2-en-1-one (39) 2. A process of preparing an aryl alkyl ether compound, comprising: reacting an aryl halide or triflate or mesylate or tosylate with an alcohol in the presence of a base, a catalyst, and a ligand to obtain an aryl alkyl ether compound. 3. The process as claimed in claim 2, wherein the catalyst is a transition metal, preferably selected from the group consisting of Pd, Pt, Ni, and combinations thereof, more preferably Pd. 4. The process as claimed in claim 2, wherein Pd is in the form of a palladium complex selected from the group consisting of tris(dibenzylideneacetone)dipalladium, tr is(dibenzylideneacetone)dipalladium chloroformadductpalladiumacetate, palladium chl oride, tetrakis(triphenylphosphine)palladium, cinnamylpalladium(II)chloridedimer, (1,5 cyclooctadiene)bis(trimethylsilylmethyl)palladium(II), allylpalladium(II)chloridedimer, bis(triphenylphosphine)palladium(II)chloride, allylpalladium(II)acetate, bi(dibenzyliden eacetone)palladium, and combinations thereof, preferably selected from the group consi sting of tris(dibenzylideneacetone) dipalladium, cinnamylpalladium(II)chloride dimer, allylpalladium(II)chloride dimer, palladium(II)acetate, and combinations thereof, more preferably tris(dibenzylideneacetone)dipalladium, cinnamylpalladium(II)chloride dimer, allylpalladium(II)acetate. 5. The process as claimed in claim 2, wherein the ligand is selected from the group consisting of BrettPhos, tBuDavePhos, RockPhos, tBuXPhos, Me4-t-BuXphos, Me3(OMe)tBuXPhos, TrixiePhos and XPhos. 6. The process as claimed in claim 2, wherein the catalyst is present in an amount in the range of 0.001 to 20 mol% with respect to at least one of the aryl halide or triflate or mesylate or tosylate and the alcohol, preferably in the range of 0.01 to 10 mol% with respect to at least one of the aryl halide or triflate or mesylate or tosylate and the alcohol, more preferably in the range of 0.1 to 5 mol% with respect to at least one of the aryl halide or triflate or mesylate or tosylate and the alcohol. 7. The process as claimed in claim 2, wherein the ligand is present in an amount in the range of 0.001 to 20 mol% with respect to the catalyst, preferably in the range of 0.01 to 10 mol% with respect to the catalyst, more preferably in the range of 0.1 to 5 mol% with respect to the catalyst. 8. The process as claimed in claim 2, wherein the reaction is carried out at a temperature in the range of 35 °C to 120 °C, preferably in the range of 50 °C to 100 °C. 9. The process as claimed in claim 2, wherein the reaction of the aryl halide or triflate or mesylate or tosylate with the alcohol is carried out in the presence of a solvent selected from the group selected consisting of polar solvent, non-polar solvent, and combination thereof, preferably toluene. 10. The process as claimed in claim 2, wherein the reaction of the aryl halide or triflate or mesylate or tosylate with the alcohol is carried out for a time in the range of 0.01 h to 24 h, preferably in the range of 0.1 h to 1h. 11. The process as claimed in claim 2, wherein the base is selected from the group consisting of NaH, KH, LiH, LiOH. H2O, K2CO3, K3PO4, K2HPO4, Na2CO3, Tl2CO3, Cs2CO3, triethylamine, and mixtures thereof, preferably Cs2CO3. 12. The process as claimed in claim 2, wherein the aryl halide or triflate or mesylate or tosylate has the formula (R1)x(A)(Z)Ar(B)m, wherein Z is selected from the group of: or; A is selected from the group consisting of heteroaryl, aryl, alkyl, cycloalkyl, heterocyclyl, wherein heteroaryl, aryl, alkyl, cycloalkyl, heterocyclyl can be optionally substituted with 1 to 9 subsituents independently selected from R1, wherein R1 is selected from the group of electron withdrawing group, electron donating group, and substituted derivatives R1 is selected from the group of alkyl, acyl, carboxylic ester, aldehydes, ketone, cyano, carboxylic acid, amide, carboxamide, nitro, phosphonic acid, sulfonic acid, halogen, pseudohalide groups, alkoxy wherein alkoxy, alkyl, acyl can be substituted with aryl, heteroaryl, alkyl, heterocycyl, halogen; B is selected from the group consisting of Cl, Br, I, triflate, mesitylate and tosylate; x is 0-9, y is 1 to 5, and m is 1-6. 13. The process as claimed in claim 12, wherein A is selected from the group of C2-C9 heteroaryl and C6-C10 aryl, wherein C2-C9 heteroaryl, C6-C10 aryl can be optionally substituted with 1 to 9 substituents independently selected from R1, wherein R1 is selected from the group of nitro, C1-C19 alkyl, C1-C19 alkoxy, wherein C1-C19 alkoxy, wherein C1- C19 alkyl can be optionally substituted with one to three C6-C10 aryl, halogen; and x is 0- 9. 14. The process as claimed in claim 2, wherein the alcohol has the formula R2-OH, wherein R2 is C1-C20 alkyl, preferably C1-C8 alkyl. 15. The process as claimed in claim 14, wherein alkyl is unsubstituted or independently substituted with up to seventeen substituents independently selected from alkyl, alkenyl, alkynyl, alkoxy, acyl, acyloxy, acylamino, amino, monoalkylamino, dialkylamino, trialkylamino, halogen, hydroxy, hydroxyalkyl, keto, thiocarbonyl, carboxy, alkylcarboxy, hydroxyamino, alkoxyamino, nitro, azido, cyano, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl and heteroarylalkyl, cycloalkenyl, cycloalkylamino, arylamino, heterocyclylamino, heteroar ylamino, cycloalkyloxy, aryloxy, heterocyclyloxy or heteroaryloxy, ethyl acetohydroxi mate, preferably fluorine. 16. The process as claimed in claim 2, wherein the molar ratio of aryl halide to alcohol is from 0.1:1 to 1:0.1. 17. The process as claimed in claim 2, wherein the reaction is carried out in the absence of oxygen.
法律状态
GRANTED
专利类型码
BA
国别省市代码
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