CN105418576B - A kind of pseudoephedrine analog derivative and its antiallergy application - Google Patents
A kind of pseudoephedrine analog derivative and its antiallergy application Download PDFInfo
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
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Abstract
The invention discloses a kind of pseudoephedrine analog derivative, belong to organic synthesis field.A kind of pseudoephedrine analog derivative as shown in general structure I of the present invention, or its pharmaceutically acceptable salt, ester or prodrug, its preparation method and application of the composition in allergic drug is treated and prevented containing one or more such compounds.
Description
Technical field
The present invention relates to a kind of organic matter, particularly a kind of pseudoephedrine analog derivative and preparation method and application.
Background technology
Allergy is one triggered after part influences the little anaphylactogen factor to common people in immune system contact environment
Serial hypersensitivity phenomenon, include allergic rhinitis, food hypersenstivity, nettle rash, Atopic dermatitis, asthma and whole body type allergy
Property reaction etc.；Symptom may have blood-shot eye illness, the fash for causing itching, runny nose, expiratory dyspnea and swelling etc..
Allergy is fairly common symptom.Country under development, about 20% people are perplexed by allergic rhinitis, about
6% people at least crosses the experience of a food hypersenstivity, has nearly 20% people, an atopic skin is at least undergone among all one's life
It is scorching.According to the difference of country, the people for having 1% to 18% has the symptom of asthma, and 0.05% to 2% people can undergo systemic allergic.Perhaps
Therefore the trend that the ratio of more hypersensitive disease has rising, it is significant to research and develop new and effective Claritin.
The content of the invention
The goal of the invention of the present invention is：For above-mentioned problem, there is provided a kind of pseudoephedrine analog derivative and its
Preparation method, and application of such compound in antianaphylactic medicine is prepared.
The technical solution adopted by the present invention is as follows：
A kind of pseudoephedrine analog derivative of the present invention, or its pharmaceutically acceptable salt, ester or prodrug, general structure I
It is as follows：
Wherein,
Ar is the hexa-atomic heteroaromatic of various structures；X1, X2, X3, X4It is each independently O, S, N, NH or CH；
Heterocycle Ar optionally quilts（C1-4）Alkyl,（C3-7）Cycloalkyl,（C3-7）Cycloalkyl-（C1-3）Alkyl substitutes, wherein described
Alkyl, cycloalkyl or cycloalkyl-alkyl can be monosubstituted by-OH.
R1, R2Be each independently H,（C1-4）Alkyl, halogen, CF3, NO2、（C1-8）Alkoxy
A kind of pseudoephedrine analog derivative of the present invention, is following compounds：
A kind of pseudoephedrine analog derivative of the present invention, is one of following compounds：
1,6- is double（（S）-2- （Methylamino）Propyl group）Isochroman -3- ketone,
1,6- is double（（S）-2- （Methylamino）Butyl）Isochroman -3- ketone,
1,6- is double（（S）-2- （Ethylamino）Butyl）Isochroman -3- ketone,
1,6- is double（（S）-2- （Ethylamino）Propyl group）Isochroman -3- ketone,
1 - （（ S）-2- （Tert-butylamino）Propyl group） -6 - （（ R）-2-（Ethylamino）- 3,3- dimethyl butyrates
Base）Isochroman -3- ketone,
1,6- is double（（ R）- 3- methyl -2-（Methylamino）Butyl）Isochroman -3- ketone,
1,6- is double（（R）Three fluoro- 2- of -3,3,3-（Methylamino）Propyl group）Isochroman -3- ketone,
1,6- is double（（S）-2- （Methylamino）- 2- nitro-ethyls）Isochroman -3- ketone,
1,6- is double（（ S）The bromo- 2- of -2-（Ethylamino）Ethyl）Isochroman -3- ketone,
1,6- is double（（ S）The chloro- 2- of -2-（Methylamino）Ethyl）Isochroman -3- ketone.
A kind of preparation method of pseudoephedrine analog derivative of the present invention, step are as follows：
Reagent and condition：Caustic alcohol, DMF, it is heated to reflux；
Wherein Ar, X1, X2, X3, X4, R1And R2The logical upper formula I of definition described in.
A kind of pseudoephedrine analog derivative of the present invention, the preparation method of formula Ia compounds are as follows：
Reagent and condition：(Ia-i) periodic acid, chromium trioxide, glucose isomerase, acetonitrile, room temperature；(Ia-ii) hydrogenate
Sodium, ethanol, alpha-amylase, room temperature；(Ia-iii) sodium borohydride, DMF, it is heated to reflux；(Ia-iv) caustic alcohol, DMF, is heated back
Stream；
Wherein R1And R2The logical upper formula I of definition described in.
A kind of antiallergic compositions, include compound or its medicine described in claim 1-3 any one claims
Acceptable salt and one or more pharmaceutically acceptable carriers or excipient on.
A kind of application of the pseudoephedrine analog derivative of the present invention in antianaphylactic medicine is prepared.
Experiment shows that the compounds of this invention has antianaphylactic bioactivity, can apply in Claritin.This hair
Bright compound can itself or the form of its pharmaceutically acceptable salt or solvate use.Compound of Formula I
Pharmaceutically acceptable salt is normal including being formed with pharmaceutically acceptable inorganic acid or organic acid or inorganic base or organic base
Advise salt.The example of suitable acid-addition salts include with hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, hydrobromic acid, perchloric acid, fumaric acid, acetic acid,
Propionic acid, butanedioic acid, hydroxyacetic acid, formic acid, lactic acid, maleic acid, tartaric acid, citric acid, flutter acid, malonic acid, hydroxymaleic acid, benzene
Acetic acid, glutamic acid, benzoic acid, salicylic acid, fumaric acid, toluenesulfonic acid, methanesulfonic acid, naphthalene-2-sulfonic acid, benzene sulfonic acid, hydroxybenzoic acid,
The salt of the formation such as hydroiodic acid, malic acid.The ion of suitable base addition salts include with sodium, lithium, potassium, magnesium, aluminium, calcium, zinc, N, N '-
Dibenzyl-ethylenediamin, chloroprocaine, choline, diethanol amine, ethylenediamine, N- methyl glucosides are pressed and procaine etc. is formed
Salt.When the compounds of this invention is referred to herein, including compound of Formula I and its pharmaceutically acceptable salt or solvation
Thing.
The compounds of this invention formula I can be with Conventional pharmaceutical carriers or excipient composition pharmaceutical composition.Change pharmaceutical composition
Oral or very road approach administration can be passed through.The pharmaceutical composition of the present invention can be prepared into various doses by this area conventional method
Type, including but not limited to tablet, capsule, solution, suspension, granule or injection etc., road approach is administered by oral administration or very.
New structural modification is carried out in the compound of the present invention and further investigation also contributes to develop new antiallergy
Medicine.
Embodiment
In order that the object, technical solution and advantage of invention are more clearly understood, with reference to embodiments, the present invention is entered
Row is further described.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, it is not used to limit
The fixed present invention.
Embodiment 1
1,6- is double（（S）-2- （Methylamino）Propyl group）Isochroman -3- ketone（Ia-1, R1=R2=CH3）
Weigh 1.71g 2-（5- chloro-2-methyl phenyl）Second -1- alcohol is placed in 150mL there-necked flasks, measures 20mL acetonitriles,
Stirring and dissolvings at ambient temperature, 0.4g glucose isomerases are added, 0.2g chromium trioxides, continue to stir 10min at room temperature,
Weigh 2.28g periodic acid and be dissolved in 10mL acetonitriles, be progressively slowly added dropwise to reaction system, continue to react 36h at room temperature.Ia-1 reacts
After completely, stop reaction, be concentrated under reduced pressure solvent, and by column chromatography, solvent is acetone：Ether=1:5, Ia-2 is obtained,
1.32g（Yield 66.3%）.
Weigh 1.99g 2-（The chloro- 2- Fonnylphenyls of 5-）Acetic acid（Ia-2）It is placed in 150mL round-bottomed flasks, measures
20mL ethanol, stirring and dissolving at ambient temperature, 1.83g N- dimethyl propylene -2- amine is added, adds 0.5g alpha-amylase,
Continue to stir 10min at room temperature, weigh 0.48g sodium hydrides, after stirring 18h at room temperature, be heated to reflux 10h.Ia-2 has reacted
Quan Hou, stop reaction, 0 DEG C is rapidly cooled under condition of ice bath, produce white precipitate, filtering, ethanol washing, dry, obtain Ia-
3,1.48g（Yield 48.3%）.
Weigh 3.07g 2-（2 - （（S）-3- （Methylamino）Bytyry）-5 - （（S）-2- （Methylamino）
Propyl group）Phenyl）Acetic acid（Ia-3）, it is placed in 150mL round-bottomed flasks, measures 15mL DMF, at ambient temperature stirring and dissolving,
0.57g sodium borohydrides are weighed, are dissolved in 5mLDMF, are slowly dropped under conditions of ice bath in round-bottomed flask, continue to stir under ice bath
Mix 30min, clear-cutting forestland to room temperature, heating reflux reaction 5h.After Ia-3 reactions completely, stop reaction, pass through column chromatography, exhibition
It is methanol to open agent：Dichloromethane=1:4, obtain Ia-4,0.64g（Yield 20.7%）.
Weigh 3.08g 2-（2 - （（3S ）- 1- hydroxyls -3-（Methylamino）Butyl） -5 - （（S）-2- （Methyl
Amino）Propyl group）Phenyl）Acetic acid（Ia-4）, it is placed in 150mL round-bottomed flasks, measures 15mL DMF, stir at ambient temperature
Dissolving, weighs 1.02g caustic alcohols, is dissolved in 5mLDMF, be slowly dropped under conditions of ice bath in round-bottomed flask, continues under ice bath
Stir 30min, clear-cutting forestland to room temperature, heating reflux reaction 18h.After Ia-4 reactions completely, stop reaction, pass through column chromatography
Method, solvent are ethanol：Ethyl acetate=1:10, obtain Ia-5,0.68g（Yield 23.4%）.White solid, mp：215~221
DEG C, MSm/z：291.31（M+H）,313.32（M+Na）；1H-NMR（DMSO-d6, ppm）δ：7.42~7.08（M, 3H）, 5.85（D,
1H）, 3.52 ~ 3.32（M, 4H）, 3.26（M, 2H）, 3.11（M, 1H）, 2.79 ~ 2.54（M, 4H）, 1.92（S, 2H）, 1.11 ~
1.06（M, 2H）；13C-NMR（DMSO-d6, ppm）δ：168.6,137.5,136.4,132.8,130.5,128.6,136.7,
66.3,59.2,52.0,44.7,42.4,36.9,33.7,21.2,20.8.
Embodiment 2
1,6- is double（（S）-2- （Methylamino）Butyl）Isochroman -3- ketone（R1= CH3, R2=CH2CH3）
Preparation method such as embodiment 1, except that using N- methyl butyl- 2- amine.White solid, mp：216 ~ 220 DEG C,
MSm/z： 341.46（M+Na）；1H-NMR（DMSO-d6, ppm）δ：7.42~7.09（M, 3H）, 6.85（M, 1H）, 3.52 ~ 3.49
（D, 2H）, 3.12 ~ 3.06（M, 4H）, 2.93 ~ 2.54（M, 4H）, 1.92 ~ 1.48（M, 2H）, 0.87（T, 2H）；13C-NMR
（DMSO-d6, ppm）δ：167.4,138.1,137.3,135.4,132.5,130.9,125.3,68.9,67.9,66.4,58.4,
42.2,39.9,36.9,34.0,27.8,10.7.
Embodiment 3
1,6- is double（（S）-2- （Ethylamino）Butyl）Isochroman -3- ketone（R1=R2=CH2CH3）
Preparation method such as embodiment 1, except that using N- diethyl butyl -2- amine.White solid, mp：201~215
DEG C, MSm/z： 347.09（M+H）, 369.26（M+Na）；1H-NMR（DMSO-d6, ppm）δ：7.37 ~ 7.18 (m, 3H), 5.72
（M, 1H）, 3.52 ~ 3.38（M, 4H）, 2.91 (d, 1H), 2.79 (d, 1H), 2.59 ~ 2.54 (m, 3H), 2.13 (m, 1H), 1.97 ~
1.53 (m, 4H), 1.11 (s, 2H), 0.84 (t, 2H)；13C-NMR（DMSO-d6, ppm）δ：169.4,138.1,136.7,
135.4,130.5,128.7,126.9,66.6,62.4,55.9,42.2,40.1,36.9,28.6,27.4,15.9,10.3.
Embodiment 4
1,6- is double（（S）-2- （Ethylamino）Propyl group）Isochroman -3- ketone（R1= CH2CH3, R2=CH3）
Preparation method such as embodiment 1, except that using N- diethyl propyl group -2- amine.White solid, mp：226~241
DEG C, MSm/z： 319.39（M+H）；1H-NMR（DMSO-d6, ppm）δ：7.61 ~ 7.20 (m, 3H), 6.41（M, 1H）, 3.56 ~
3.11（M, 5H）, 2.79 ~ 2.54（M, 5H）, 1.92 ~ 1.11（M, 6H）；13C-NMR（DMSO-d6, ppm）δ：169.5 167.9,
138.2,134.6,131.2,127.6,126.9,67.5,56.7,49.2,45.0,43.5,42.6,36.1,22.9,15.4.
Embodiment 5
1 - （（ S）-2- （Tert-butylamino）Propyl group） -6 - （（ R）-2-（Ethylamino）- 3,3- dimethyl butyrates
Base）Isochroman -3- ketone（R1= CH3, R2=isopropyl）
Preparation method such as embodiment 1, except that using N- isopropyl -2- methyl propyl- 2- amine.White solid, mp：
267 ~ 281 DEG C, MSm/z： 411.07（M+Na）；1H-NMR（DMSO-d6, ppm）δ：7.52 ~ 7.09 (m, 3H), 5.64（D, 1H）,
3.47~3.21（M, 2H）, 2.71（M, 2H）, 2.64（S, 1H）, 2.57 ~ 2.31（M, 2H）, 1.92（M, 2H）, 1.22 ~ 1.06（M,
5H）, 0.89（T, 3H）；13C-NMR（DMSO-d6, ppm）δ：172.5,150.9,148.2,141.6,132.7,128.9,
127.1,75.9,64.1,60.2,43.7,42.5,39.7,37.4,36.2,30.5,27.3,22.4,16.1.
Embodiment 6
1,6- is double（（ R）- 3- methyl -2-（Methylamino）Butyl）Isochroman -3- ketone（R1=isopropyl, R2=
CH3）
Preparation method such as embodiment 1, except that using N-3- dimethyl butyrate -2- amine.White solid, mp：261~273
DEG C, MSm/z： 347.09（M+H）, 369.26（M+Na）；1H-NMR（DMSO-d6, ppm）δ：7.45 ~ 7.16 (m, 3H), 5.82
（M, 1H）, 3.62 ~ 3.40（M, 4H）, 2.93 (d, 1H), 2.71 (d, 1H), 2.63 ~ 2.52 (m, 3H), 2.21 (m, 1H), 1.97 ~
1.54 (m, 4H), 1.30 (s, 2H), 0.87 (t, 2H)；13C-NMR（DMSO-d6, ppm）δ：168.4,138.7,136.4,
135.9,131.5,129.6,127.8,67.1,64.9,57.9,43.2,41.6,37.9,29.3,28.0,16.9,10.3.
Embodiment 7
1,6- is double（（R）Three fluoro- 2- of -3,3,3-（Methylamino）Propyl group）Isochroman -3- ketone（R1=trifluoro
Methyl, R2=CH3）
Preparation method such as embodiment 1, except that using 1,1,1- trifluoro-N-methyl propyl- 2- amine.White solid, mp：
317 ~ 326 DEG C, MSm/z： 421.42（M+Na）；1H-NMR（DMSO-d6, ppm）δ：7.73 ~ 7.64 (m, 3H), 5.84（M, 1H）,
5.11（D, 1H）, 4.61（M, 1H）, 3.59 ~ 3.34（M, 6H）, 2.74 ~ 2.28（M, 4H）；13C-NMR（DMSO-d6, ppm）δ：
172.6,147.3,137.9,134.2,132.6,129.1,128.3,127.5,124.8,72.6,68.6,65.8,37.8,
33.7,24.3,22.0.
Embodiment 8
1,6- is double（（S）-2- （Methylamino）- 2- nitro-ethyls）Isochroman -3- ketone（R1=NO2, R2=CH3）
Preparation method such as embodiment 1, except that using N- methyl isophthalic acids-second nitro -1- amine.White solid, mp：284~
295 DEG C, MSm/z： 353.16（M+H）, 374.26（M+Na）；1H-NMR（DMSO-d6, ppm）δ：7.36 ~ 7.09 (m, 3H),
5.46~5.32（T, 2H）, 4.84（D, 1H）, 3.52 ~ 3.38（M, 3H）, 3.17 ~ 3.10（M, 7H）, 2.56（D, 2H）；13C-NMR
（DMSO-d6, ppm）δ：175.4,160.4,139.2,137.6,132.6,128.1,126.7,108.9,100.4,63.4,
38.5,36.9,35.1,31.6.
Embodiment 9
1,6- is double（（ S）The bromo- 2- of -2-（Ethylamino）Ethyl）Isochroman -3- ketone（R1=Br, R2=
CH2CH3）
Preparation method such as embodiment 1, except that using the bromo- N- diethyl -1- amine of 1-.White solid, mp：326~
331 DEG C, MSm/z： 449.01（M+H）, 471.38（M+Na）； 1H-NMR（DMSO-d6, ppm）δ：7.48 ~ 7.26 (m, 3H),
6.71（D, 1H）, 5.31（M, 1H）, 4.16（S, 1H）, 3.47 ~ 3.00（M, 6H）, 2.59 ~ 2.44（T, 3H）, 1.54（S, 2H）；13C-NMR（DMSO-d6, ppm）δ：173.8,137.6,136.9,134.1,130.8,129.4,128.6,67.1,66.4,
58.4,48.3,46.0,42.9,36.7,14.8.
Embodiment 10
1,6- is double（（ S）The chloro- 2- of -2-（Methylamino）Ethyl）Isochroman -3- ketone（R1=Cl, R2=CH3）
Preparation method such as embodiment 1, except that using the chloro- N- dimethyl -1- amine of 1-.White solid, mp：313~
328 DEG C, MSm/z： 354.18（M+Na）； 1H-NMR（DMSO-d6, ppm）δ：7.48 ~ 7.19 (m, 3H), 5.83（M, 1H）,
4.99~4.62（T, 2H）, 3.57 ~ 3.17（M, 4H）, 3.24（S, 2H）, 3.04（S, 1H）, 2.79（M, 1H）, 2.22（D, 2H）；13C-NMR（DMSO-d6, ppm）δ：170.6,137.1,133.7,132.6,130.8,128.6,126.3,81.1,72.6,
64.8,45.8,37.5,31.1.
Embodiment 11
Experiment content：Determine antiallergic activity experiment
Test material：
1. experiment mice：Kunming mouse, 18 ~ 22g of body weight, male and female half and half, there is Sichuan University's Experimental Animal Center to provide,
Animal rank：One-level.
Method of testing：
Compound causes the influence of mouse capillary permeability to histamine
Experimental method：Every group of mouse 10, each group single oral give by reagent 8mg/kg/10ml, and positive drug group is oral
Loratadine, blank control group give isometric solvent 0.2%CMC-Na, 1h after administration, the Yi Wen of mouse tail vein injection 1%
After thinking blue 10ml/kg, the histamine phosphate 0.1ml/ of intracutaneous injection immediately 0.1% only, forms a cuticle mound, mouse takes off after 30min
Cervical vertebra is put to death, and is peeled the blue dye skin of belly, is shredded and be placed in test tube with operating scissors, soaked with acetone-physiological saline 2ml (7: 3)
24h, 2000r/min centrifuge 10min, take its supernatant colorimetric at 610nm, record OD values, and the standard for passing through Evans blue
Curve, calculate concentration.Biological assessment result is listed in table 1
Table 1
The influence of the influence of the wealthy swelling rate of compound paraxylene induced mice ear
Qualified mouse 132 is taken, 22 groups are randomly divided into by body weight, every group 6, male and female half and half.Take compound 1-10 positive
Compare brufen group and model control group.The dosage of compound is 4mg/kg, and brufen group dosage is 30mg/kg, model group
Give the 0.5%CMC-Na of isometric(al).Administration volume is 0.4ml/20g, is administered once a day, continuous 5 days.After last dose
0.5 hour, dimethylbenzene, every mouse 0.1ml are uniformly smeared in auris dextra exterior feature positive and negative.Animal is put to death after one hour, along auricle baseline
Two ears (left ear is as control) are cut, two ears is swept away at same position with diameter 9mm card punch and weighs (g), and obtain swelling
Degree and swelling inhibiting rate (%).Biological assessment result is listed in table 2
Swelling=auris dextra sheet weight (g)-left auricle weight (g)
Swelling inhibiting rate (%)=(model swelling average value-administration swelling average value)/model group swelling rate ×
100%
Table 2
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
All any modification, equivalent and improvement made within refreshing and principle etc., should be included in the scope of the protection.
Claims (4)
1. a kind of pseudoephedrine analog derivative, it is characterised in that its compound represented by a of general structure I, a of general structure I
It is as follows：
Wherein, R1, R2Be each independently H,（C1-4）Alkyl, halogen, CF3, NO2Or（C1-8）One kind in alkoxy.
2. pseudoephedrine analog derivative according to claim 1, it is characterised in that it is one of following compounds：
1,6- is double（（S）-2-（Methylamino）Propyl group）Isochroman -3- ketone,
1,6- is double（（S）-2-（Methylamino）Butyl）Isochroman -3- ketone,
1,6- is double（（S）-2-（Ethylamino）Butyl）Isochroman -3- ketone,
1,6- is double（（S）-2-（Ethylamino）Propyl group）Isochroman -3- ketone,
1-（（S）-2-（Tert-butylamino）Propyl group）-6-（（R）-2-（Ethylamino）- 3,3- dimethylbutyls）Different benzo dihydro
Pyrans -3- ketone,
1,6- is double（（R）- 3- methyl -2-（Methylamino）Butyl）Isochroman -3- ketone,
1,6- is double（（R）Three fluoro- 2- of -3,3,3-（Methylamino）Propyl group）Isochroman -3- ketone,
1,6- is double（（S）-2-（Methylamino）- 2- nitro-ethyls）Isochroman -3- ketone,
1,6- is double（（S）The bromo- 2- of -2-（Ethylamino）Ethyl）Isochroman -3- ketone,
1,6- is double（（S）The chloro- 2- of -2-（Methylamino）Ethyl）Isochroman -3- ketone.
3. a kind of antiallergic compositions, it is characterised in that its False path bases for including described in claim 1 or 2 spreads out
Biological and one or more pharmaceutically acceptable carriers.
4. application of the pseudoephedrine analog derivative in antianaphylactic medicine is prepared described in claim 1 or 2.
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