CN103980206A - Pyrimidine ethylamine compound and preparation method thereof - Google Patents
Pyrimidine ethylamine compound and preparation method thereof Download PDFInfo
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- CN103980206A CN103980206A CN201410228691.0A CN201410228691A CN103980206A CN 103980206 A CN103980206 A CN 103980206A CN 201410228691 A CN201410228691 A CN 201410228691A CN 103980206 A CN103980206 A CN 103980206A
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- compound
- pyrimidine
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- cyclopropyl
- ethylamine
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- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- -1 Pyrimidine ethylamine compound Chemical class 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 239000002994 raw material Substances 0.000 claims abstract description 12
- 229940125782 compound 2 Drugs 0.000 claims abstract description 8
- 229940125898 compound 5 Drugs 0.000 claims abstract description 8
- 229940126214 compound 3 Drugs 0.000 claims abstract description 7
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims abstract description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229940073608 benzyl chloride Drugs 0.000 claims abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- 150000003230 pyrimidines Chemical class 0.000 claims abstract description 3
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 claims abstract description 3
- SVJDAWOBQMNUJN-UHFFFAOYSA-N N1=CN=CC=C1.C(C)N Chemical class N1=CN=CC=C1.C(C)N SVJDAWOBQMNUJN-UHFFFAOYSA-N 0.000 claims description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 3
- 229940125904 compound 1 Drugs 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 claims description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 4
- 229910000564 Raney nickel Inorganic materials 0.000 abstract description 2
- UXIICOJHCSNIEL-UHFFFAOYSA-N 2-(2-cyclopropylpyrimidin-5-yl)ethanamine Chemical compound N1=CC(CCN)=CN=C1C1CC1 UXIICOJHCSNIEL-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- FXFPOKGPAPEJNE-UHFFFAOYSA-N cyclopropanecarboximidamide Chemical compound NC(=N)C1CC1 FXFPOKGPAPEJNE-UHFFFAOYSA-N 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- IIHQNAXFIODVDU-UHFFFAOYSA-N pyrimidine-2-carbonitrile Chemical compound N#CC1=NC=CC=N1 IIHQNAXFIODVDU-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000001514 detection method Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 206010039491 Sarcoma Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- HFEXWDPGIAJVAJ-UHFFFAOYSA-N CCC(C)c1ncc(CCN)cn1 Chemical compound CCC(C)c1ncc(CCN)cn1 HFEXWDPGIAJVAJ-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a pyrimidine ethylamine compound and a preparation method thereof. The compound is 2-(2-cyclopropyl)-pyrimidine-5-ethylamine. The preparation method comprises the following steps: (1) with cyclopropyl formamidine as a starting material, alkalifying by sodium ethoxide; reacting with a compound B to obtain a pyrimidine derivative compound 2; (2) deacidifying the compound 2 at high temperature to obtain a compound 3 and benzyl chloride; (3) inserting carbonyl in the compound 3 to obtain a derivative compound (4) of pyrimidine methyl ester; (4) reducing the compound 4 by DIBAL-H (Diisobutylaluminum hydride) to obtain a compound 5; (5) chloridizing the compound 5 by thionyl chloride to obtain a compound 6; (6) reacting the compound 6 with NaCN to obtain a derivative compound (7) of cyanopyrimidine; and (7) catalyzing and hydrogenating the compound 7 by raney nickel to obtain a target product 8. According to the preparation method, raw materials are low in price and the synthesis method is simple; the preparation method is suitable for large-scale industrial production.
Description
Technical field
The present invention relates to production of chemicals field, especially a kind of pyrimidine ethylamine compounds and preparation method thereof.
Background technology
Pyrimidine ethylamine compounds is widely used in drug molecule, and with the derivative of this compou nd synthesis, in treatment cancer, cardiovascular and nervous system disorders aspect has huge clinical medicine using value.With this compound, do parent and can further synthesize more complicated derivative, for studying more widely such compound property, provide condition.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of pyrimidine ethylamine compounds.
Another technical problem to be solved by this invention is to provide the preparation method of above-mentioned pyrimidine ethylamine compounds.
For solving the problems of the technologies described above, technical scheme of the present invention is:
A pyrimidine ethylamine compounds, 2-(2-cyclopropyl)-pyrimidine-5-ethamine, its structural formula is shown in (I),
Preferably, above-mentioned pyrimidine ethylamine compounds, the proterties of 2-(2-cyclopropyl)-pyrimidine-5-ethamine is liquid, its proton nmr spectra data are 1H-NMR (DMSO; 400HZ) 2.00 (m, 4H) 2.147 (m, 1H) 2.560 (t, 2H) 2.746 (t, 2H) 8.473 (s, 2H).
The preparation method of above-mentioned pyrimidine ethylamine compounds, concrete steps are as follows:
(1) take compound 1 cyclopropyl carbonamidine is starting raw material, does alkali, with compd B at sodium ethylate
reaction obtains compound 2, is pyrimidine derivatives;
(2) compound 2 high temperature depicklings obtain compound 3 and benzyl chloride;
(3) compound 3 is inserted carbonyl and is obtained compound 4, is the derivative of pyrimidine methyl esters;
(4) compound 4 obtains compound 5 by diisobutyl aluminium hydride (DIBAL-H) reduction;
(5) compound 5 obtains compound 6 with the sub-maple chlorination of dichloro;
(6) compound 6 reacts with NaCN and obtains compound 7, is the derivative of pyrimidine cyano group;
(7) through raney ni catalysis, hydrogenation obtains target product compound 8 to compound 7, wherein,
Preferably, the preparation method of above-mentioned pyrimidine ethylamine compounds, described compound 6,7, as intermediate product, is new compound.
The preparation method's of above-mentioned pyrimidine ethylamine compounds concrete reaction equation is as follows:
The invention has the beneficial effects as follows:
The preparation method of above-mentioned pyrimidine ethylamine compounds, raw material is cheap, and synthetic method is simple, is applicable to the needs that large-scale industrial is produced.
Accompanying drawing explanation
Fig. 1 is the HNMR spectrogram of 2-(2-cyclopropyl)-pyrimidine-5-ethamine.
Embodiment
In order to make those skilled in the art better understand technical scheme of the present invention, below in conjunction with embodiment, technical scheme of the present invention is described in further detail.
Embodiment 1
As shown in Figure 1, the preparation method of 2-(2-cyclopropyl)-pyrimidine-5-ethamine, concrete steps are as follows:
(1), between 45 ℃ to 50 ℃, the 270ml ethanolic soln of 196.2g compound 1 cyclopropyl carbonamidine and 2M sodium ethylate are slowly splashed into 90g compd B simultaneously
450ml ethanolic soln in (1h drips complete), it's weekend then keep to past 45 ℃-50 ℃; After 60h, TLC detects, and raw material disappears, and system is spin-dried for, and with 500ml frozen water, processes, and drips concentrated hydrochloric acid to PH=2 at 5 ℃, filters out solid and obtains compound 2, dries and obtains crude product 65g; TLC information: raw material Rf=0.6, product Rf=0.3, developping agent: MeOH (methyl alcohol): DCM (methylene dichloride)=1:10.
(2) 65g compound 2 is dropped in dimethylbenzene to 140 ℃ of backflow 2h; TLC detection reaction is complete, is spin-dried for solvent, crosses column purification (sherwood oil: ethyl acetate=20:1) obtain 34.4g compound 3 sterlings, two step yields 16.15%.TLC information: raw material Rf=0.3, product Rf=0.8, developping agent: methylene dichloride: methyl alcohol=1:10.
(3) by 34.4g compound 3,1.7g Pd (dppf) Cl
2, 35g TEA (trolamine) and 650mlMeOH drop in autoclave together, and carbon monoxide displacement 3 times, then passes into CO gas to 1.0MPa, is then warming up to 110 ℃, reaction overnight 14h; After 17h, TLC detection reaction is complete, and system is cooled to room temperature, filters the system that is spin-dried for, and crude product is crossed column purification (sherwood oil: ethyl acetate=5:1) obtain 27g sterling compound 4, yield 87.7%.TLC information: raw material Rf=0.6, product Rf=0.4, developping agent: sherwood oil: ethyl acetate=5:1.
(4) at-50 ℃, DIBAL-H (diisobutyl aluminium hydride) is splashed in the anhydrous tetrahydrofuran solution of 27g compound 4,2.5h dropwises, and then slowly returns to 0 ℃; TLC detection reaction stops, and slowly drops into 2N NaOH (500ml) at 0 ℃ to system, and PH is adjusted to 11, system ethyl acetate extraction (200ml * 3), and organic phase is dry, is spin-dried for to obtain 11g crude product compound 5, yield 48.3%.TLC information: raw material Rf=0.7, product Rf=0.3, developping agent: methylene dichloride: methyl alcohol=10:1.
(5) 10g compound 5 is dissolved in 100ml DCM, under normal temperature, splashes into thionyl chloride (20min dropwises), is warming up to 45 degree backflows (1h); TLC detection reaction stops, and system is spin-dried for, and then uses saturated Na
2cO
3solution is adjusted to 9 by system PH, system ethyl acetate extraction (200ml * 3), and organic phase is dry, is spin-dried for to obtain 8.7g compound 6, yield 70.4%.TLC information: raw material Rf=0.2, product Rf=0.8, developping agent: sherwood oil: ethyl acetate=1:1.
(6) 8.2g compound 6 is dissolved in 82ml DMSO (dimethyl sulfoxide (DMSO)), under normal temperature, adds 2.87gNaCN, is warming up to 50 ℃ of reaction 3h; TLC detection reaction stops, and system is poured in 300ml water, is then extracted with ethyl acetate (100ml * 3), and organic phase saturated common salt water washing is dry, is spin-dried for, and crosses silicagel column (200-300 order silica gel pillar) and obtains 5.1g compound 7, yield 58.7%.(PE:EA＝5:1)。TLC information: raw material Rf=0.7, product Rf=0.5, developping agent: sherwood oil: ethyl acetate=2:1;
(7) by 5.1g compound 7,0.03g Raney's nickel, 5.1mL ammoniacal liquor and 200mL methyl alcohol drop into autoclave, and hydrogen exchange 3 times, passes into hydrogen to 1.0MPa, and reacts 2h at 70 ℃; TLC detection reaction stops, and filters, and system is spin-dried for, and crosses silicagel column (500 grams of 200-300 order silica gel pillars) and obtains 3.4g compound 8, yield 65.0%.TLC information: raw material Rf=0.8, product Rf=0.2, developping agent: methylene dichloride: methyl alcohol=20:1.
The structural confirmation of compound 8,1H-NMR (DMSO; 400HZ) 2.00 (m, 4H) 2.147 (m, 1H) 2.560 (t, 2H) 2.746 (t, 2H) 8.473 (s, 2H).
Application test example
With small white mouse, do anti-tumor experiment, 8 mouse oxter inoculation S180 sarcoma cells, make mouse source sarcoma model.After embodiment 1 gained 100mg compound is dissolved in 20ml propylene glycol solution and is dissolved, then carry out intratumor injection after adding the dilution of 30ml water for injection, 0.5 milliliter every, once a day, drug treatment is 7 days, and test-results shows, average tumour inhibiting rate is 73%.
Above-mentioned detailed description of this kind of pyrimidine ethylamine compounds and preparation method thereof being carried out with reference to embodiment; illustrative rather than determinate; can list several embodiment according to institute's limited range; therefore in the variation and the modification that do not depart under general plotting of the present invention, within should belonging to protection scope of the present invention.
Claims (4)
1. a pyrimidine ethylamine compounds, is characterized in that: be 2-(2-cyclopropyl)-pyrimidine-5-ethamine, its structural formula is shown in (I),
2. pyrimidine ethylamine compounds according to claim 1, is characterized in that: the yellow liquid of described 2-(2-cyclopropyl)-pyrimidine-5-ethamine, and its proton nmr spectra data are H-NMR (DMSO; 400HZ) 2.00 (m, 4H) 2.147 (m, 1H) 2.560 (t, 2H) 2.746 (t, 2H) 8.473 (s, 2H).
3. the preparation method of the pyrimidine ethylamine compounds described in claim 1 or 2, is characterized in that: concrete steps are as follows:
(1) take compound 1 cyclopropyl carbonamidine is starting raw material, does alkali, with compound at sodium ethylate
reaction obtains compound 2, is pyrimidine derivatives;
(2) compound 2 high temperature depicklings obtain compound 3 and benzyl chloride;
(3) compound 3 is inserted carbonyl and is obtained compound 4, is the derivative of pyrimidine methyl esters;
(4) compound 4 is reduced and is obtained compound 5 by diisobutyl aluminium hydride;
(5) compound 5 obtains compound 6 with the sub-maple chlorination of dichloro;
(6) compound 6 reacts with NaCN and obtains compound 7, is the derivative of pyrimidine cyano group;
(7) through raney ni catalysis, hydrogenation obtains target product compound 8 to compound 7, wherein,
4. the preparation method of pyrimidine ethylamine compounds according to claim 3, is characterized in that: described compound 6,7, as intermediate product, is new compound.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107205392A (en) * | 2015-01-30 | 2017-09-26 | 巴斯夫欧洲公司 | The phenyl pyrimidine class of weeding |
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2014
- 2014-05-27 CN CN201410228691.0A patent/CN103980206B/en active Active
Non-Patent Citations (2)
| Title |
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| STN: ""STN REGISTRY 数据库"", 《STN REGISTRY 数据库》, 17 August 2007 (2007-08-17) * |
| 赵培亮等: ""具有抗肿瘤活性的嘧啶类化合物研究进展"", 《药学学报》, vol. 47, no. 5, 31 December 2012 (2012-12-31), pages 580 - 587 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107205392A (en) * | 2015-01-30 | 2017-09-26 | 巴斯夫欧洲公司 | The phenyl pyrimidine class of weeding |
| JP2018505168A (en) * | 2015-01-30 | 2018-02-22 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Herbicidal phenylpyrimidine |
| AU2016212053B2 (en) * | 2015-01-30 | 2019-09-19 | Basf Se | Herbicidal phenylpyrimidines |
| US10420341B2 (en) | 2015-01-30 | 2019-09-24 | Basf Se | Herbicidal phenylpyrimidines |
| EP3250034B1 (en) * | 2015-01-30 | 2020-03-11 | Basf Se | Herbicidal phenylpyrimidines |
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