CN103833587B - One kettle way prepares the method for high unsaturated fatty acyl Propanolamine - Google Patents
One kettle way prepares the method for high unsaturated fatty acyl Propanolamine Download PDFInfo
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- CN103833587B CN103833587B CN201410113528.XA CN201410113528A CN103833587B CN 103833587 B CN103833587 B CN 103833587B CN 201410113528 A CN201410113528 A CN 201410113528A CN 103833587 B CN103833587 B CN 103833587B
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- -1 fatty acyl Propanolamine Chemical compound 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 26
- 241000195493 Cryptophyta Species 0.000 claims abstract description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 125000005456 glyceride group Chemical group 0.000 claims abstract description 18
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 14
- 238000010992 reflux Methods 0.000 claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 9
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 9
- 238000007127 saponification reaction Methods 0.000 claims description 8
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 238000010523 cascade reaction Methods 0.000 claims description 4
- MBMBGCFOFBJSGT-KUBAVDMBSA-N docosahexaenoic acid Chemical group CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 3
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 3
- PIFPCDRPHCQLSJ-WYIJOVFWSA-N 4,8,12,15,19-Docosapentaenoic acid Chemical compound CC\C=C\CC\C=C\C\C=C\CC\C=C\CC\C=C\CCC(O)=O PIFPCDRPHCQLSJ-WYIJOVFWSA-N 0.000 claims description 2
- PIFPCDRPHCQLSJ-UHFFFAOYSA-N Clupanodonic acid Natural products CCC=CCCC=CCC=CCCC=CCCC=CCCC(O)=O PIFPCDRPHCQLSJ-UHFFFAOYSA-N 0.000 claims description 2
- HXWJFEZDFPRLBG-UHFFFAOYSA-N Timnodonic acid Natural products CCCC=CC=CCC=CCC=CCC=CCCCC(O)=O HXWJFEZDFPRLBG-UHFFFAOYSA-N 0.000 claims description 2
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical group CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- DVSZKTAMJJTWFG-UHFFFAOYSA-N docosa-2,4,6,8,10,12-hexaenoic acid Chemical group CCCCCCCCCC=CC=CC=CC=CC=CC=CC(O)=O DVSZKTAMJJTWFG-UHFFFAOYSA-N 0.000 claims description 2
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 2
- IQLUYYHUNSSHIY-HZUMYPAESA-N eicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O IQLUYYHUNSSHIY-HZUMYPAESA-N 0.000 claims description 2
- 235000021290 n-3 DPA Nutrition 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000741 silica gel Substances 0.000 abstract description 5
- 229910002027 silica gel Inorganic materials 0.000 abstract description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 1
- 238000013375 chromatographic separation Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010606 normalization Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000008431 aliphatic amides Chemical class 0.000 description 3
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- 208000032928 Dyslipidaemia Diseases 0.000 description 1
- 208000017170 Lipid metabolism disease Diseases 0.000 description 1
- 108010084311 Novozyme 435 Proteins 0.000 description 1
- 102000023984 PPAR alpha Human genes 0.000 description 1
- 108010028924 PPAR alpha Proteins 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of method that one kettle way prepares high unsaturated fatty acyl Propanolamine, the method is included in reaction flask and adds algae oil glyceride, Propanolamine, triethylamine, KOH reaction solution successively, adopt one kettle way reflux, direct preparation high unsaturated fatty acyl Propanolamine compound, through normal pressure silica gel column chromatographic separation, the total content of product height unsaturated fatty acyl Propanolamine is more than 96%.The inventive method has the advantage that syntheti c route is short, technique simple, easy handling, reaction conditions are gentle, preparation cost is low, is the efficient method easily of the high unsaturated fatty acids amides of preparation.
Description
Technical field
The invention belongs to chemosynthesis technical field, relate to a kind of preparation method of high unsaturated fatty acids amides, especially relate to a kind of one kettle way and clean the method preparing high unsaturated fatty acyl Propanolamine.
Background technology
Unsaturated fatty acids amides is the derivative of fatty acid be extensively present in animal body, they are the important biologically active substances of a class, not still a kind of endogenous grease, very high to the avidity of PPAR α, and less to the side effect of human body, can be used for reducing fat, treatment dyslipidemia (D Pi Nuomeili, Chinese patent, 2004, publication number CN1523982A; Greenwald, P.EuropeanJournalofCancer2001,37,948-965).
The synthetic method of the high unsaturated fatty acids acid amides reported mainly contains the following two kinds:
(1) algae oil glyceride is as initial feed, and first is that saponification reagent prepares free unsaturated fatty acid with KOH, and recycling unsaturated fatty acids and aliphatic amide react (Wu Keke under the effect of immobilized lipase Novozym435, Chinese oil, 2002,23,91-93).Namely this technique generates high unsaturated fatty acyl Propanolamine through two-step reaction, and syntheti c route is as follows:
(2) algae oil glyceride is as initial feed, and first is that saponification reagent prepares free unsaturated fatty acid with KOH, recycling halide reagent (SOCl
2or (COCl)
2) activated carboxyl generation acyl chlorides, as nucleophilic reagent attack acyl chlorides, there is condensation reaction (Jin Xin, Chinese patent, 200710009268.1) in aliphatic amide.Namely this technique also generates high unsaturated fatty acyl Propanolamine through two-step reaction, and syntheti c route is as follows:
In sum, the synthetic method of current unsaturated fatty acids amides is: algae oil glyceride is under KOH effect, and first carry out saponification reaction and obtain free unsaturated fatty acid, then unsaturated fatty acids and aliphatic amide carry out condensation reaction.This method just will can obtain target product through two steps, synthesis technique relative complex, and reaction conditions is harsher, and meanwhile, also need organic solvent as solvent, cost is high, unfriendly to environment.
Summary of the invention
In view of the deficiencies in the prior art, the object of the invention is to by lot of experiments research and persistent exploration, provide a kind of one kettle way to prepare the method for high unsaturated fatty acyl Propanolamine, the solvent toxicity that the method adopts is little, and reaction conditions is gentle, preparation environmental friendliness.
The object of the present invention is achieved like this:
A kind of one kettle way prepares the method for high unsaturated fatty acyl Propanolamine; the method is under the condition of reflux; algae oil glyceride adds in the reaction solution containing KOH saponification reaction occurs; generate free unsaturated fatty acids intermediate; unsaturated fatty acids again under the effect of organic bases with Propanolamine generation acylation reaction; realize one kettle way cascade reaction, obtain target product height unsaturated fatty acyl Propanolamine, chemical reaction is as follows:
Preferably, one kettle way described above prepares the method for high unsaturated fatty acyl Propanolamine, and wherein saponification reaction and acylation reaction merge to carry out continuously.
Preferably, the method for one kettle way height unsaturated fatty acyl Propanolamine described above, the temperature of wherein said reflux is 45 ~ 90 DEG C, is preferably 60 ~ 90 DEG C.
Preferably, one kettle way described above prepares the method for high unsaturated fatty acyl Propanolamine, and the time of wherein said reflux is 1 ~ 4 hour.
Preferably, one kettle way described above prepares the method for high unsaturated fatty acyl Propanolamine, and wherein said reaction solution selects water, methyl alcohol or ethanol, the mass ratio (0.7 ~ 1.0) of described reaction solution and algae oil glyceride: 1.0.
Preferably, one kettle way described above prepares the method for high unsaturated fatty acyl Propanolamine, and wherein said KOH consumption and the mass ratio of algae oil glyceride are (0.12 ~ 0.18): 1.0.
Preferably, one kettle way described above prepares the method for high unsaturated fatty acyl Propanolamine, the at least one in triethylamine, diethylamine, hexahydropyridine and N-methylmorpholine selected by wherein said organic bases, the mass ratio (0.48 ~ 0.72) of described organic bases and algae oil glyceride: 1.0.
Preferably, one kettle way described above prepares the method for high unsaturated fatty acyl Propanolamine, the volume mass ratio (0.32 ~ 0.45) of wherein said Propanolamine and algae oil glyceride: 1.0.
Further preferably, one kettle way described above prepares the method for high unsaturated fatty acyl Propanolamine, and wherein R is the unsaturated fatty chain of timnodonic acid, docosahexenoic acid, eicosatetraenoic acid and clupanodonic acid.
The reaction product solution that one kettle way cascade reaction of the present invention obtains is refined as follows: reaction product solution is cooled to room temperature, adds saturated NaHCO
3/ CH
2cl
2(volume ratio 1: 1) aqueous solution extracts, and leaves standstill, and releases lower floor's organic phase, adds anhydrous MgSO
4drying, filter, vacuum rotary steam, obtain high unsaturated fatty acyl Propanolamine crude product, normal pressure column chromatography, obtains sterling.
Compared with existing preparation technology, the advantage that the present invention has and progressive as follows:
(1) the cascade reaction step of saponification reaction and acylation reaction realizes in one pot, and easy handling, reaction conditions are gentle.
(2) one pot reaction can carry out in aqueous phase, avoids using oxalyl chloride as halide reagent, thus avoids the use of organic solvent, and avoids discharging the destruction of HCl gas to surrounding environment.
(3) cheaper starting materials is easy to get, and syntheti c route is short, and cost is low.
Accompanying drawing explanation
Fig. 1 is the HPLC spectrogram of high unsaturated fatty acyl Propanolamine product prepared by embodiment 1.
Embodiment
Be below specific embodiments of the invention, processing step of the present invention and parameter thereof are done to describing further, but protection scope of the present invention be not limited to these embodiments.Every do not deviate from the present invention's design change or equivalent substituting include within protection scope of the present invention.
Embodiment 1: 100g algae oil glyceride is joined in 75mL water, then add KOH15g, triethylamine 60g, Propanolamine 37mL successively, stir in emulsion.This emulsion, under 60 DEG C of oil bath constant temperatures, heats 2 hours.After reaction solution is cooled to room temperature, add the saturated NaHCO of 500mL
3/ CH
2cl
2(volume ratio 1: 1) aqueous solution extracts, and leaves standstill, and releases lower floor's organic phase.Add anhydrous MgSO
4drying, filter, vacuum rotary steam, obtains high unsaturated fatty acyl Propanolamine crude product.Normal pressure column chromatography, 2kg400 order silica gel is placed in 8cm diameter glass chromatography column, sherwood oil profit post, sherwood oil: ethyl acetate=1: 1 (v: v) wash-out, obtain product 18.2g, it is 96.3% that the total content of high unsaturated fatty acyl Propanolamine calculates (HPLC) through area normalization method.
HPLC condition: chromatographic column: HypersilODS2 (4.6*250mm, 5 μm), flow velocity 1 μ L/min, moving phase: water/acetonitrile=4/6 (v/v) determined wavelength: 205nm, sampling volume 5 μ L, column temperature: 25 DEG C (other embodiment is also same).
Note: through the further analysis of Waters High Performance Liquid Chromatography/Mass Spectrometry HPLC-MS coupling technique, can t be determined
1/2=9.03min (content 7.12%) is eicosa-pentaenoic acyl Propanolamine, i.e. EPA Propanolamine; t
1/2=11.41min is two dodecahexaene acyl Propanolamines (content 85.29%), i.e. DHA Propanolamine; t
1/2=15.09min is Eicosatetraenoic acyl Propanolamine (content 3.77%), i.e. ARA Propanolamine, t
1/2=17.55min is docosapentaenoic acyl Propanolamine (content 0.18%), i.e. DPA Propanolamine.Therefore the total content of unsaturated fatty acyl Propanolamine is 96.3% in product.
Embodiment 2: 200g algae oil glyceride is joined in 160mL methyl alcohol, then add KOH30g, triethylamine 144g, Propanolamine 80mL successively, stir in emulsion.This emulsion, under 90 DEG C of oil bath constant temperatures, heats 2 hours.After reaction solution is cooled to room temperature, add the saturated NaHCO of 800mL
3/ CH
2cl
2(volume ratio 1: 1) aqueous solution extracts, and leaves standstill, and releases lower floor's organic phase.Add anhydrous MgSO
4drying, filter, vacuum rotary steam, obtains high unsaturated fatty acyl Propanolamine crude product.Normal pressure column chromatography, 4kg400 order silica gel is placed in 8cm diameter glass chromatography column, sherwood oil profit post, sherwood oil: ethyl acetate=1: 1 (v: v) wash-out, obtain product 36.5g, it is 96.8% that the total content of high unsaturated fatty acyl Propanolamine calculates (HPLC) through area normalization method.
Embodiment 3: 100g algae oil glyceride is joined in 100mL methyl alcohol, then add KOH12g, triethylamine 48g, Propanolamine 44mL successively, stir in emulsion.This emulsion, under 75 DEG C of oil bath constant temperatures, heats 4 hours.After reaction solution is cooled to room temperature, add the saturated NaHCO of 400mL
3/ CH
2cl
2(volume ratio 1: 1) aqueous solution extracts, and leaves standstill, and releases lower floor's organic phase.Add anhydrous MgSO
4drying, filter, vacuum rotary steam, obtains high unsaturated fatty acyl Propanolamine crude product.Normal pressure column chromatography, 2kg400 order silica gel is placed in 8cm diameter glass chromatography column, sherwood oil profit post, sherwood oil: ethyl acetate=1: 1 (v: v) wash-out, obtain product 16.3g, it is 97.5% that the total content of high unsaturated fatty acyl Propanolamine calculates (HPLC) through area normalization method.
Embodiment 4: 100g algae oil glyceride is joined in 75mL water, then add KOH18g, N-methylmorpholine 72g, Propanolamine 37mL successively, stir in emulsion.This emulsion, under 75 DEG C of oil bath constant temperatures, heats 2 hours.After reaction solution is cooled to room temperature, add the saturated NaHCO of 500mL
3/ CH
2cl
2(volume ratio 1: 1) aqueous solution extracts, and leaves standstill, and releases lower floor's organic phase.Add anhydrous MgSO
4drying, filter, vacuum rotary steam, obtains high unsaturated fatty acyl Propanolamine crude product.Normal pressure column chromatography, 2kg400 order silica gel is placed in 8cm diameter glass chromatography column, sherwood oil profit post, sherwood oil: ethyl acetate=1: 1 (v: v) wash-out, obtain product 17.6g, it is 96.5% that the total content of high unsaturated fatty acyl Propanolamine calculates (HPLC) through area normalization method.
Claims (2)
1. an one kettle way prepares the method for high unsaturated fatty acyl Propanolamine; it is characterized in that: under the condition of reflux; algae oil glyceride adds in the reaction solution containing KOH saponification reaction occurs; generate free unsaturated fatty acids intermediate; unsaturated fatty acids again under the effect of organic bases with Propanolamine generation acylation reaction; realize one kettle way cascade reaction, obtain target product height unsaturated fatty acyl Propanolamine, chemical reaction is as follows:
saponification reaction and acylation reaction merge to carry out continuously, the temperature of described reflux is 45 ~ 90 DEG C, the time of described reflux is 1 ~ 4 hour, described reaction solution selects water, methyl alcohol or ethanol, the mass ratio of described reaction solution and algae oil glyceride is 0.7 ~ 1.0: 1.0, described KOH consumption and the mass ratio of algae oil glyceride are 0.12 ~ 0.18: 1.0, triethylamine selected by described organic bases, diethylamine, at least one in hexahydropyridine and N-methylmorpholine, the mass ratio of described organic bases and algae oil glyceride is 0.48 ~ 0.72: 1.0, described Propanolamine is 0.32 ~ 0.45: 1.0 with the volume mass ratio of algae oil glyceride, R is timnodonic acid, docosahexenoic acid, the unsaturated fatty chain of eicosatetraenoic acid and clupanodonic acid.
2. a kind of one kettle way prepares the method for high unsaturated fatty acyl Propanolamine as claimed in claim 1, it is characterized in that: the temperature of described reflux is 60 ~ 90 DEG C.
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| US4619938A (en) * | 1984-03-21 | 1986-10-28 | Terumo Kabushiki Kaisha | Fatty acid derivatives of aminoalkyl nicotinic acid esters and platelet aggregation inhibitors |
| CN100999482A (en) * | 2006-11-28 | 2007-07-18 | 王伟松 | Method for synthesizing fatty acid diethanolamide |
| CN101108811A (en) * | 2007-07-24 | 2008-01-23 | 厦门大学 | A method for synthesizing amine derivatives of oleic acid |
| CN102295573A (en) * | 2011-07-12 | 2011-12-28 | 厦门大学 | Chemical synthetic method of oleoylethanolamide |
| WO2012149352A1 (en) * | 2011-04-29 | 2012-11-01 | Catabasis Pharmaceuticals, Inc. | Fatty acid guanidine and salicylate guanidine derivatives and their uses |
| CN103113253A (en) * | 2013-01-28 | 2013-05-22 | 国家海洋局第三海洋研究所 | Alcohol amine derivative of unsaturated fatty acid and preparation method and application thereof |
| WO2013158302A1 (en) * | 2012-04-16 | 2013-10-24 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Derivatives of docosahexaenoylethanolamide and uses thereof |
-
2014
- 2014-03-26 CN CN201410113528.XA patent/CN103833587B/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4619938A (en) * | 1984-03-21 | 1986-10-28 | Terumo Kabushiki Kaisha | Fatty acid derivatives of aminoalkyl nicotinic acid esters and platelet aggregation inhibitors |
| CN100999482A (en) * | 2006-11-28 | 2007-07-18 | 王伟松 | Method for synthesizing fatty acid diethanolamide |
| CN101108811A (en) * | 2007-07-24 | 2008-01-23 | 厦门大学 | A method for synthesizing amine derivatives of oleic acid |
| WO2012149352A1 (en) * | 2011-04-29 | 2012-11-01 | Catabasis Pharmaceuticals, Inc. | Fatty acid guanidine and salicylate guanidine derivatives and their uses |
| CN102295573A (en) * | 2011-07-12 | 2011-12-28 | 厦门大学 | Chemical synthetic method of oleoylethanolamide |
| WO2013158302A1 (en) * | 2012-04-16 | 2013-10-24 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Derivatives of docosahexaenoylethanolamide and uses thereof |
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