手性药物有哪些举例.docx
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手性药物有哪些举例.docx
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手性药物有哪些举例
手性药物有哪些举例
【篇一:
手性药物有哪些举例】
>
acohnhchohclf3cch3n
hn
coohd-maleicacid
或
hclonhclch3
f3c
linezolid吗啉恶酮:
抗菌药
no2nhoffohnphch2ococlnahco3onfno2(i-pr)2etnnfhco2nh4pd/cooocooch2phh3cbuliooomeso2clet3nonfonomsnan3nfnonfoonohnfnh2
oon3
ooh2pd/confonnh2ac2onf
on
o
hno
ch3
lisofylline:
促造血药
oh3cbh3cobrohohobobrch2cl2buli
clobo
clbrli
zncl2
clobobr
memgbr
och3bobrna2co3h2o2h3chnohobrch3nah
ch3nn
o
ohh3con
o
ch3nn
ch3
robalzotan:
抗抑郁药
omenh2oomebr2obrphnofphpd/chcoonh4foohnofohclohnoffsocl2foclnofnh3o(cf3so2)2of3csoonofnh2noco,meohpd(oac)2ooomenonh2phch2brk2co3broomenphph
ome
omenh2onabh3cn
omenof
bbr3
rotigotine:
抗帕金森症
oh
me2so4naohome
ome1)na/etoh2)hcl/h2oomehn
o
1)prnh22)h2/pt
ohhn
ch3
1)l-dbta2)resolution
ch3
hbr
hn
ch3
omech3ns
ome
oh
hoo
s
ch3hcl/ethernshcl
me3n/bh3
ohoh
talampanel:
抗癫痫药
ch3och3o2nohchooooch3
oo
chiralreduction
oo
oo2/naohdmf/dmsoo
ch3oohh2n
hn
ch3och3oonohhn
no2och3mscl
no2
no2ch3onnpd/cch3oonnoch
3
ch3oonomshnoch3naohoo
ch3
no2
no2
nh2
tonabersat:
抗偏头痛
oh3cohhcch3chcl3oh3cooonh3etohh3conh2ohch3ch3et3nh3coclclohnoohch3ch3fcldastch2cl2h3coch3ch3onoh3co2.5mol/lh2so4ohnoohchch33clfmnch3ch3fcl
3+
ocatalysth3co
o
chch33
f
atorvastatincalcium阿托发他汀钙:
降血脂药
hoooohfch3nch3ohnca2+
2r1no
ohonc
oeth3co
r1n
ldar2r1=ome,r2=mehonc
o
r2
et2bomenabh4
r1hohonconr2
h3comeh3comeh3ch3cooo
r1nr2h2,ra-ni
r1h3ch3cooonr2
meso3h
nc
nh2
fooch3ch3ohnheatf
h3ch3c
ooo
r1n
r2
ho
r1nooh
r2
n
ch3ch3ohn
hcl
fnch3ch3ohn
ho1)naoh2)ca(ac)2
oooh
f
n
ch3ch3o
ca2+
hn
2
moxifloxacinhydrochloride盐酸莫西沙星:
喹诺酮类抗菌药
ofhnnomeoohhcl
oohoholialh4hnnac2o
oono
h2nn
onoh2,pd/c
hn
ono
n
1)l-(+)tartaricacidmotherliquors2)crystallization
1)naoh2)d-(-)tartaricacid3)crystallization4)naoh
cis-racemichnnh2,pd/chnnh
(s,s)-isomer
offomeoffomech3fooofclko
o
ooch3ffomenh2
o
ooch3ch(oet)3ac2o
et3n
f
offomef
oonhch3
ch3
1)naf2)h+
ooffomenoohfhnnh1)base2)hclhnnome
oohhcl
flesinoxanhydrochloride:
抗高血压
oonnfhnohcloh
oohepichlorohydrinek2co3,dmf
so2cl2ch2cl2
cl
ooh
hno3ch2cl2
cl
oohno2
cl
oono2o
1)hcl,c3h7oh2)koh,etoh
cl
oono2
oh
phcoclch2cl2
ocloono2ooonnho1)resolution(+)-camphorsulfonicacid2)benzoylaziridine3)koh,etoh4)hcl,etohnh2oh2-pd/c,etohoohclo
ohn(ch2ch2cl)2hclphcl
oonn
ohhclf
hcl
hno
implitapide:
降血脂
ch3nh3cnonhoh
ch3nh3cnh2i-prch2ch2onohclch3npdheath3cnhih3c
ch3ch3nclnh2-nh2h3cch3heatnnhnh2oh3cnnh
brh3ch3cooht-buohdcch3coot-but-buokoot-bu
nbs,aibn
br
oot-buiich3h2so4h3cnoot-bunnooh
ch3t-buoki+iih3cn
ch3nh2nohh3cnonhoh
1)hobt,edc2)chormatography
瑞伐托酯:
支气管扩张药
ooohso
n
ch3
ooclohsldach3ohsch3meohh2so4
oosch3ch3ho
n
nah
oos
n(ch2o)nnahch3
oos
hnchromatographyoversio2ch3oh
oos
nf3cooh
oh
ch3
o
nhplcosch3o
ooohso
n
oh
sio2
ch3
盐酸咪达普利:
抗高血压
h3c
o
och3nhonh3ct-buohichohc3och3ch3k2co3oh3cnoonohhcl
oohnn
oooh
oohnn
o
on
oohc3och3ch3
pd/c,h2
oh3cn
hn
ohc3och3ch3i
ch3ohoome
p-tsclet3ntso
ch3oomech3otsoohc3och3ch3naohtso
ch3oohh3c
socl2tso
ch3oiicl
o
oet3nnh2
t-buoki+ii
oh3cn
n
h3c
o
och3nhoh3cnnoohc3och3ch3hclh3co
och3nhonh3coonohhcl
左布比卡因:
局部麻醉药
1
路
线
ch3hoonh2nhch3
socl2tol
ch3
hnoch3
bubrk2co3nh
ch3
hnoch3
1)(s,s)-tartaricacid2))hcl3
ch3
结
晶
n
hnoch3
异
丙
醇
n
2
路
线
nh2nano2hoonhcooch2phacoh,aconahoonh
oacdcccooch2phch3nh2ch3ohk2co3tsclhnoch3otsk2co3ch3hnoch3nhcooch2ph
oacch3hnch3o
nh
cooch2ph
ch3
ch3
hnoch3
bubrk2co3nh
ch3
hnoch3
nh
cooch2ph
n
etoh
belaperidone抗精神病
ohfmgclthfohhclclftolfhnfhclacetonehvresolutionhnioohhbrnhnobriifh2n
cooch3nh2
h2nclcooch3k2co3cooch3nhcooch3
foi+iinhnon
孟鲁司特钠抗过敏
oclnhbrmgch2tol/thfclnohch2
brh3coodmfpd(oac)2clnh3cooohclnh3cmeso2cl(i-pr)2netcltolacetonitrilenh3chooooso2meich3memgclcecl3/thfohclnh3choocdibthf
ch3
ohohcn
(i-pr)2soorsocl2ch2cl2
osoocooh
nacnch2cl2ho
cnmeso2clmeso2o
cn
mecosk
naohacstolh2o
iihs
o
oh
1)bulii+ii2)hncln
s
h3cho
ch3
mkc-242抗抑郁
h3coch3oooch2ph
h3c
ooh
tsclpyr
h3c
oots
nah
acoh
h3co
h3co
ohoch2phhoooch2phooohtsclet3ndmaptsoooch2photsh2pd/c
tsoooh
ots
k2co3
otsi
oonobrhoonah
onoo
oon2h4
oh2nooiiooi+iionhoohcl
escitalopramoxalate抗抑郁
1
路
线
ncmgbrncooffncomgbrch3omgclnch3ncacohohohoomgbr
nc
omgbrclmgo
ch3nch3
fch3nch3
ch3ocf3phclo
fch3ocf3phncoohohplc
fch3ocf3phncooho
ch3nch3
ch3nch3
t-buok
fnconch3ch3
f
f
2
路
线
ohosocl2oosocl2h3ch3conooh3ch3conohohch3nch3cl
ooofbrmg
h3cch3honh2
oh3cch3honh
oo
h3ch3c
onohclmgoch3nch3
tartaricacidcsa
h3ch3c
on
fohohch3nch3
fh3ch3conoch3nch3pocl3nconch3ch3f
meso2clet3n
f
f
aliskirenfumarate
hoh3co
oh
k2co3br
meo
oh3co
oh
me3sibrmeo
o
meo
brh3c
lihmdsch3onooh3cobrh3cch3ph
omeooh3coh3comennch3omech3bulimeooh3conch3omench3omech3h3c1)hcl2)(t-buoco)2ooch3nophlioh,h2o2meooh3co
o1)nabh4,i2oh2)pph3,nbsmeoh3cch3
omemeooh3cooh3chncoot-buch3dibal
omeooh3cohh3chncoot-buch3
h3cbrmg
ch3ophmeooh3co
h3cch3ohohncoot-buch3
ph
h3ch3co
ch3och3
h3c
1)tsoh2)chromatography
h3ct-buoconmeooh3co
ch3
h3cch3oo
phh2,pd/cmeooh3co
h3ct-buocon
ch3
h3cch3ooh
1)nmmo,ptap2)kmno4,tbab
h3c
ch3
h3c
ch3
h3c
ch3
h3co
ch3h3cch3nh2ohh2noo(eto)2pocnteameooh3coh3cohch3ch3hh3cnnh2oohooccoohh3ct-buocon
ch3
t-buoconmeooh3co
h3co
ch3ch3hh3cnh2noo1)hcl2)fumaricacid
h3c
ch3
h3c
ch3
meo
oh3conh2ch3
h3c
2
中间体合成路线ch3oh3conolihmdsphbrh3co(cocl)2ch3och3oo(cocl)2cloch3ch3clooch3ch31)phch2oh,tea2)choromatographyoophoch3ch3och3oh2,pd/chooooso4nophhoooch3ch3ooch3ch3naio4rucl3
ooho
aprepitant止吐药
cf3cf3onfol-selectridethf,-78ocnfohclothf
o
cf3
on
oo
f
cf3
cf3
cp2time2
on
o
cf3ch2
1)h2,pd/c,etoac,i-proh2)chromatographicseparation
cf3o
fcf3clcnh3cnh2nhco2menaomeclh3coocnhnnh2h3coonfxylene,heatohnhnnnfocf3h3coof
cf3
cf
3
hn
onhh2n
h2no
hn
onh2cloch2ph
naoh,0oc
h2no
hn
onhoch2ph
naoh,refluxcf3
o
hnhnn
och2phh2,pd/c,hcoonh4o
hnhnn
oh
socl2
o
hnhnn
clh3conhfocf3
cf3h3confo
cf3
o
hnhnn
ezetimibe降血脂
ohoh
f
no
f
oohldaoofnho
oohhnaio4nof
oohcnofoch3fli,tms-clfootsohnfoffohohbh3cbsfofnofh2,pd/coch2otmsfofohticl4ooho
n
n
nh2ohohcoh3coobu3nclh3conofo(cocl)2clnofo1)zncl2fooliohhonomgbrok2co3phch2brohcofn
o
f
o
f
2)chiralhplc
oocbsbh3noffooh
o
f
nf
ohpd/c,h2fofoh
n
fk-888抗哮喘
hn(t-buoco)2ohh2noet3nooohnhoh3chobtwscoonhoch3n
hclch3nh2no
oh3ch3ch3conohhobtwsco
oohoh3ch3ch3conohonhch3no
oh
hclohnohnhch3nonch3hobtwsconnohch3onhnoch3
reboxetine瑞波西汀抗抑郁
ohhohoch2ch3ohomshopnboch2ch3ohhonhcloohooch2ch3ohohhohoch2ch3ohohh
och2ch3oho
och2ch3ohhonh2
och2ch3ohonh
och2ch3ohonh
tadalafilpde5inhibitor
coomecoomenhnh3clanhoocoomenhoono6o
12an
nh2clb
5-hclo
12an
cl
c
nho
6n
do
1o(cialis)
nho
6n
o2o(epi-cialis)
coomecoomeanhl-tryptophanmethylesterhydrochloridenh3cl95%nhnhb94%
oo2
coome
33
coomecnh
1n
nh
1n
obnoo71%
obndoo96%
o3acoome
3
4a
o
coome
3
nh
1nh
e92%oo5coome
3
nh
1nh
f93%oo6
12a6n
on
nh
1n
cloo
ref.2095%
nh
oo
o7
otadalafil1
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