CN105859810A - Closed-ring byproduct I of 1-(2-deoxidatoin-beta-ribofuranose-based)-5-iodine-2-pyrmodone and preparing method of closed-ring byproduct I - Google Patents
Closed-ring byproduct I of 1-(2-deoxidatoin-beta-ribofuranose-based)-5-iodine-2-pyrmodone and preparing method of closed-ring byproduct I Download PDFInfo
- Publication number
- CN105859810A CN105859810A CN201610242419.7A CN201610242419A CN105859810A CN 105859810 A CN105859810 A CN 105859810A CN 201610242419 A CN201610242419 A CN 201610242419A CN 105859810 A CN105859810 A CN 105859810A
- Authority
- CN
- China
- Prior art keywords
- beta
- pyrimidone
- deoxidation
- iodo
- ribofuranosyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention relates to 1-(2-deoxidatoin-beta-ribofuranose-based)-5-iodine-2-pyrmodone, in particular to a closed-ring byproduct I of 1-(2-deoxidatoin-beta-ribofuranose-based)-5-iodine-2-pyrmodone and a preparing method of the closed-ring byproduct I. The XRPD reflection angle of the closed-ring byproduct I reaches characteristic peaks at 11.13 +/-0.2 degrees, 14.54 +/-0.2 degrees, 16.98 +/-0.2 degrees, 19.69 +/-0.2 degrees, 19.87 +/-0.2 degrees, 21.59 +/-0.2 degrees, 23.55 +/-0.2 degrees, 25.61 +/-0.2 degrees, 28.69 +/-0.2 degrees, 34.97 +/-0.2 degrees and 38.43 +/-0.2 degrees. Guidance is provided for studying the stability of 1-(2-deoxidatoin-beta-ribofuranose-based)-5-iodine-2-pyrmodone.
Description
Technical field
The present invention relates to 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone, be specifically related to a kind of 1-(2-deoxidation-beta-furan
Mutter ribosyl) the cyclization by-product I of-5-iodo-2-pyrimidone and preparation method thereof.
Background technology
1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone (IPdR) is the precursor of IUdR medicine, initially by as anti-
Virus drugs is studied, and is presently believed to be a kind of potential oral TdR radiosensitizer, and IPdR can mix the swollen of fast breeding
In oncocyte, the normal structure of fast breeding such as bone marrow and enterocyte also have incorporation.1994, Cheng et al. was nude mice
Dorsal sc injection people source colon cancer cell (HCT-116), thus set up tumor model it was confirmed this assumes.IPdR is as list
Medicine is used for treating lymphadenomatous I phase in late period clinic and completed (NCT01240577) in 2012, as the 0 of tumour radiotherapy sensitizer
Phase clinic completed in NIH in 2013, reached expected results.
IPdR structural formula is as follows:
But, there is many problems in IPdR in terms of stability, particularly in high temperature, aqueous or alcohol system, once drops
Solve formation by-product and will affect the using effect of IPdR.The most also find no the report in terms of the IPdR by-product of pass.
Summary of the invention
It is an object of the invention to provide the cyclization by-product I of a kind of 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone, for
The stability of research 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone provides and instructs, and present invention simultaneously provides it the easiest
OK, it is easy to accomplish preparation method.
The cyclization by-product I of 1-of the present invention (2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone, its nuclear magnetic resonance, NMR number
According to as follows:
1H NMR (400MHz, DMSO) δ 9.28 (d, J=5.3Hz, 3H), 8.82 (d, J=3.1Hz, 1H), 8.69 (d, J
=3.1Hz, 1H), 6.66 (d, J=5.4Hz, 3H), 6.05 (t, J=5.9Hz, 1H), 5.86 (d, J=5.4Hz, 3H), 5.43 (s,
3H), 5.39 5.26 (m, 2H), 5.16 (d, J=4.3Hz, 3H), 4.32 4.18 (m, 7H), 4.01 3.84 (m, 4H), 3.84
3.39 (m, 66H), 3.57 3.39 (m, 60H), 3.49 3.39 (m, 60H), 2.47 2.30 (m, 4H), 2.16 (dtd, J=9.8,
6.6,3.3Hz,4H)。
Angle of reflection 2 θ of its X-ray powder diffraction figure at 11.13 ± 0.2 °, 14.54 ± 0.2 °, 16.98 ± 0.2 °, 19.69 ± 0.2 °,
19.87 ± 0.2 °, 21.59 ± 0.2 °, 23.55 ± 0.2 °, 25.61 ± 0.2 °, 28.69 ± 0.2 °, 34.97 ± 0.2 °, at 38.43 ± 0.2 °
There is characteristic peak.
The preparation method of the cyclization by-product I of described 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone is divided into following two
Kind:
One, first method:
1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone is dissolved in solvent, stirring, filters, take filtrate and be positioned over tool
Have in the container that the sealed membrane of passage seals, be placed under room temperature condition and volatilize, separate out solid.
Wherein:
Solvent is the mixture of acetonitrile and methanol, and both volume ratios are 1:3.
1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone is 3:0.2～0.3 with the ratio of solvent, 1-(2-deoxidation-beta-
Ribofuranosyl)-5-iodo-2-pyrimidone quality is in terms of mg, and solvent volume is in terms of ml.
Whipping temp 40～60 DEG C, mixing time 1～3h.
Two, second method:
Being dissolved in solvent by 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone, filter, under stirring, in filtrate, dropping is anti-
Solvent separates out solid, or is transferred under room temperature condition separate out solid by the filtrate separated out without solid after dropping anti-solvent.
Wherein:
Solvent is methanol.
Anti-solvent is ethyl acetate, butanone or methyl tertiary butyl ether(MTBE).
1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone is 1:0.05～0.1 with the ratio of solvent, 1-(2-deoxidation-beta-
Ribofuranosyl)-5-iodo-2-pyrimidone quality is in terms of mg, and solvent volume is in terms of ml.
Solvent is 1～2:5～10 with the volume ratio of anti-solvent.
Beneficial effects of the present invention is as follows:
The present invention prepares cyclization by-product I, and the stability for research 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone carries
Having supplied to instruct, the preparation method of the present invention is simple, it is easy to accomplish.
Accompanying drawing explanation
Fig. 1 is the nuclear magnetic resonance, NMR figure of (2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone cyclization by-product I of 1-in embodiment 1；
Fig. 2 is the x-ray powder of (2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone cyclization by-product I of 1-in embodiment 1
Diffraction pattern；
Fig. 3 is the nuclear magnetic resonance, NMR figure of 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone crystal formation A；
Fig. 4 is the X-ray powder diffraction figure of 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone crystal formation A；
Fig. 5 is the x-ray powder of (2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone cyclization by-product I of 1-in embodiment 4
Diffraction pattern；
Fig. 6 is the x-ray powder of (2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone cyclization by-product I of 1-in embodiment 5
Diffraction pattern；
Fig. 7 is the x-ray powder of (2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone cyclization by-product I of 1-in embodiment 6
Diffraction pattern.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described further.
Embodiment 1
The preparation method of the cyclization by-product I of described 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone:
Weigh 1-(2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone of 15mg in 3ml bottle, add the second of 1.0ml
Nitrile and the mixture of methanol, wherein, acetonitrile is 1:3 with the volume ratio of methanol, after being placed in 50 DEG C of stirring 2h, crosses leaching clarification
Liquid, equipped with the bottle of settled solution and pricks 5～6 apertures with ParafilmTM above, places and the most slowly volatilizees.3
After it, collecting gained solid, and carry out nuclear magnetic resonance, NMR, X-ray powder diffraction XRPD, result is as shown in Figure 1 and Figure 2.
The nuclear magnetic resonance data of cyclization by-product I is as follows:
1H NMR (400MHz, DMSO) δ 9.28 (d, J=5.3Hz, 3H), 8.82 (d, J=3.1Hz, 1H), 8.69 (d, J
=3.1Hz, 1H), 6.66 (d, J=5.4Hz, 3H), 6.05 (t, J=5.9Hz, 1H), 5.86 (d, J=5.4Hz, 3H), 5.43 (s,
3H), 5.39 5.26 (m, 2H), 5.16 (d, J=4.3Hz, 3H), 4.32 4.18 (m, 7H), 4.01 3.84 (m, 4H), 3.84
3.39 (m, 66H), 3.57 3.39 (m, 60H), 3.49 3.39 (m, 60H), 2.47 2.30 (m, 4H), 2.16 (dtd, J=9.8,
6.6,3.3Hz,4H).
The X-ray powder diffraction data of cyclization by-product I are as shown in table 1 below:
The XRPD data peak of table 1 cyclization by-product I
Meanwhile, the crystal formation (named crystal formation A) to 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone original state
Carry out nuclear magnetic resonance, NMR, X-ray powder diffraction, as shown in Figure 3,4.
Crystal formation A nuclear magnetic resonance data is as follows:
1H NMR (400MHz, DMSO) δ 8.75 (d, J=3.1Hz, 1H), 8.63 (d, J=3.1Hz, 1H), 5.98 (t, J=
5.9Hz, 1H), 5.33 5.18 (m, 2H), 4.28 4.16 (m, 1H), 3.88 (q, J=3.4Hz, 1H), 3.64 (dddd, J=45.7,
12.0,4.8,3.4Hz, 2H), 2.34 (ddd, J=13.4,6.3,5.1Hz, 1H), 2.10 (dt, J=13.4,5.9Hz, 1H).
The X-ray powder diffraction data of crystal formation A are as shown in table 2 below:
The XRPD data peak of table 2 crystal formation A
By Fig. 1-4 and table 1-2 it is clear that crystal formation A and cyclization by-product I has obvious difference.
Embodiment 2
The preparation method of the cyclization by-product I of described 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone:
Weigh 1-(2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone of 15mg in 3ml bottle, add the second of 1.5ml
Nitrile and the mixture of methanol, wherein, acetonitrile is 1:3 with the volume ratio of methanol, after being placed in 40 DEG C of stirring 3h, crosses leaching clarification
Liquid, equipped with the bottle of settled solution and pricks 5～6 apertures with ParafilmTM above, places and the most slowly volatilizees, and 3
After it, collect gained solid.
Embodiment 3
The preparation method of the cyclization by-product I of described 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone:
Weigh 1-(2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone of 15mg in 3ml bottle, add the second of 1.0ml
Nitrile and the mixture of methanol, wherein, acetonitrile is 1:3 with the volume ratio of methanol, after being placed in 60 DEG C of stirring 1h, crosses leaching clarification
Liquid, equipped with the bottle of settled solution and pricks 5～6 apertures with ParafilmTM above, places and the most slowly volatilizees.3
After it, collect gained solid.
Embodiment 4
The preparation method of the cyclization by-product I of described 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone:
Weigh 1-(2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone of 20mg in 3ml bottle, add the first of 2.0ml
Alcohol, filters, and drips ethyl acetate 10ml under stirring in filtrate, and the filtrate separated out without solid after dropping anti-solvent is transferred to room
Solid is separated out under the conditions of temperature.And carrying out X-ray powder diffraction XRPD detection, result is as shown in Figure 5.Cyclization by-product I penetrates
Line powder diffraction data is as shown in table 3 below:
The XRPD data peak of table 3 cyclization by-product I
| 2theta | D is spaced | Intensity % |
| 6.615447 | 13.36145 | 7.60 |
| 11.131700 | 7.94865 | 22.47 |
| 12.506250 | 7.07794 | 7.08 |
| 14.543730 | 6.09063 | 10.68 |
| 16.984690 | 5.22042 | 13.20 |
| 19.693930 | 4.50795 | 18.95 |
| 19.871080 | 4.46816 | 9.69 |
| 21.586430 | 4.11682 | 100.00 |
| 22.577780 | 3.93826 | 7.62 |
| 23.553770 | 3.77723 | 53.30 |
| 24.543490 | 3.62711 | 1.25 |
| 25.605110 | 3.47908 | 7.04 |
| 26.659060 | 3.34389 | 1.96 |
| 27.150960 | 3.28441 | 1.86 |
| 28.687770 | 3.11187 | 13.74 |
| 31.893100 | 2.80606 | 6.05 |
| 32.529980 | 2.75256 | 4.36 |
| 32.918160 | 2.72098 | 4.23 |
| 33.911620 | 2.64351 | 1.39 |
| 34.973270 | 2.56566 | 6.28 |
| 36.434470 | 2.46605 | 4.56 |
| 37.600080 | 2.39224 | 1.63 |
| 38.194910 | 2.35634 | 4.00 |
| 38.433460 | 2.34226 | 4.50 |
Embodiment 5
The preparation method of the cyclization by-product I of described 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone:
Weigh 1-(2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone of 20mg in 3ml bottle, add the first of 2.0ml
Alcohol, filters, and drips butanone 10ml under stirring in filtrate, and the filtrate separated out without solid after dropping anti-solvent is transferred to room temperature bar
Solid is separated out under part.And carrying out X-ray powder diffraction XRPD detection, result is as shown in Figure 6.Cyclization by-product I ray
Powder diffraction data is as shown in table 4 below:
The XRPD data peak of table 4 cyclization by-product I
Embodiment 6
The preparation method of the cyclization by-product I of described 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone:
Weigh 1-(2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone of 20mg in 3ml bottle, add the first of 2.0ml
Alcohol, filters, and drips methyl tertiary butyl ether(MTBE) 10ml, separate out solid under stirring in filtrate.And carry out X-ray powder diffraction XRPD
Detection, result is as shown in Figure 7.Cyclization by-product I ray powder diffraction data is as shown in table 5 below:
The XRPD data peak of table 5 cyclization by-product I
| 2theta | D is spaced | Intensity % |
| 11.119020 | 7.95769 | 28.17 |
| 14.521190 | 6.10004 | 18.69 |
| 16.954950 | 5.22951 | 30.19 |
| 18.952840 | 4.68251 | 5.58 |
| 19.700490 | 4.50647 | 29.63 |
| 21.240600 | 4.18306 | 33.94 |
| 21.583060 | 4.11746 | 100.00 |
| 23.555410 | 3.77697 | 38.57 |
| 24.612870 | 3.61704 | 54.47 |
| 25.602700 | 3.47941 | 9.18 |
| 26.817310 | 3.32451 | 27.82 |
| 27.215830 | 3.27673 | 44.87 |
| 28.683420 | 3.11233 | 19.59 |
| 32.548150 | 2.75106 | 9.19 |
| 35.200240 | 2.54963 | 3.59 |
Claims (12)
1. the cyclization by-product I of 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone, it is characterised in that: its nuclear-magnetism
Resonance data is as follows:
1H NMR (400MHz, DMSO) δ 9.28 (d, J=5.3Hz, 3H), 8.82 (d, J=3.1Hz, 1H), 8.69 (d, J
=3.1Hz, 1H), 6.66 (d, J=5.4Hz, 3H), 6.05 (t, J=5.9Hz, 1H), 5.86 (d, J=5.4Hz, 3H), 5.43 (s,
3H), 5.39 5.26 (m, 2H), 5.16 (d, J=4.3Hz, 3H), 4.32 4.18 (m, 7H), 4.01 3.84 (m, 4H), 3.84
3.39 (m, 66H), 3.57 3.39 (m, 60H), 3.49 3.39 (m, 60H), 2.47 2.30 (m, 4H), 2.16 (dtd, J=9.8,
6.6,3.3Hz,4H)。
The cyclization by-product I of 1-the most according to claim 1 (2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone, its
Be characterised by: angle of reflection 2 θ of its X-ray powder diffraction figure at 11.13 ± 0.2 °, 14.54 ± 0.2 °, 16.98 ± 0.2 °, 19.69 ± 0.2 °,
19.87 ± 0.2 °, 21.59 ± 0.2 °, 23.55 ± 0.2 °, 25.61 ± 0.2 °, 28.69 ± 0.2 °, 34.97 ± 0.2 °, at 38.43 ± 0.2 °
There is characteristic peak.
3. the system of the cyclization by-product I of 1-(2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone described in a claim 1
Preparation Method, it is characterised in that: 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone is dissolved in solvent, stirring, filters,
Take in the container that filtrate is positioned over the sealed membrane sealing with passage, be placed under room temperature condition and volatilize, separate out solid.
The system of the cyclization by-product I of 1-the most according to claim 3 (2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone
Preparation Method, it is characterised in that: solvent is the mixture of acetonitrile and methanol.
The system of the cyclization by-product I of 1-the most according to claim 4 (2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone
Preparation Method, it is characterised in that: acetonitrile is with the mixture of methanol, and both volume ratios are 1:3.
The system of the cyclization by-product I of 1-the most according to claim 3 (2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone
Preparation Method, it is characterised in that: 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone is 3:0.2～0.3 with the ratio of solvent,
-5-iodo-2-pyrimidone quality is in terms of mg for 1-(2-deoxidation-beta-ribofuranosyl), and solvent volume is in terms of ml.
The system of the cyclization by-product I of 1-the most according to claim 3 (2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone
Preparation Method, it is characterised in that: whipping temp 40～60 DEG C, mixing time 1～3h.
8. the system of the cyclization by-product I of 1-(2-deoxidation-beta-the ribofuranosyl)-5-iodo-2-pyrimidone described in a claim 1
Preparation Method, it is characterised in that: 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone is dissolved in solvent, filters, stirring
The lower anti-solvent that drips in filtrate separates out solid, or the filtrate separated out without solid after dropping anti-solvent is transferred under room temperature condition
Separate out solid.
The system of the cyclization by-product I of 1-the most according to claim 8 (2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone
Preparation Method, it is characterised in that: solvent is methanol.
The cyclization by-product I's of 1-the most according to claim 8 (2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone
Preparation method, it is characterised in that: anti-solvent is ethyl acetate, butanone or methyl tertiary butyl ether(MTBE).
The cyclization by-product I's of 11. 1-according to claim 8 (2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone
Preparation method, it is characterised in that: the ratio of 1-(2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone and solvent be 1:0.05～
-5-iodo-2-pyrimidone quality is in terms of mg for 0.1,1-(2-deoxidation-beta-ribofuranosyl), and solvent volume is in terms of ml.
The cyclization by-product I's of 12. 1-according to claim 8 (2-deoxidation-beta-ribofuranosyl)-5-iodo-2-pyrimidone
Preparation method, it is characterised in that: solvent is 1～2:5～10 with the volume ratio of anti-solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610242419.7A CN105859810A (en) | 2016-04-19 | 2016-04-19 | Closed-ring byproduct I of 1-(2-deoxidatoin-beta-ribofuranose-based)-5-iodine-2-pyrmodone and preparing method of closed-ring byproduct I |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610242419.7A CN105859810A (en) | 2016-04-19 | 2016-04-19 | Closed-ring byproduct I of 1-(2-deoxidatoin-beta-ribofuranose-based)-5-iodine-2-pyrmodone and preparing method of closed-ring byproduct I |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105859810A true CN105859810A (en) | 2016-08-17 |
Family
ID=56632370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610242419.7A Pending CN105859810A (en) | 2016-04-19 | 2016-04-19 | Closed-ring byproduct I of 1-(2-deoxidatoin-beta-ribofuranose-based)-5-iodine-2-pyrmodone and preparing method of closed-ring byproduct I |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105859810A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4895937A (en) * | 1982-01-05 | 1990-01-23 | The Research Foundation Of State University Of New York | 5-ioso-2-pyrimidinone nucleoside |
-
2016
- 2016-04-19 CN CN201610242419.7A patent/CN105859810A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4895937A (en) * | 1982-01-05 | 1990-01-23 | The Research Foundation Of State University Of New York | 5-ioso-2-pyrimidinone nucleoside |
Non-Patent Citations (1)
| Title |
|---|
| SIMON M. N. EFANGE，等: "Synthesis and Biological Activities of 2-Pyrimidinone Nucleosides. 2. 5-Halo-2-pyrimidinone 2’-Deoxyribonucleosides", 《J. MED. CHEM.》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2017208215A1 (en) | Stable crystal form of tipiracil hydrochloride and crystallization method for the same | |
| AU2020401223A1 (en) | Compositions and methods for substituted 7-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine analogs as inhibitors of KRAS | |
| CN110088088A (en) | The novel crystal forms and preparation method thereof of { [5- (3- chlorphenyl) -3- pyridone -2- carbonyl] amino } acetic acid | |
| CN104080777B (en) | As the morpholinyl-derivatives of MOGAT-2 inhibitor | |
| CN103896970A (en) | 2-Pyridinemethanol copper complex as well as preparation method and application | |
| CN102167718B (en) | 16-imidazole substitute-3amine substitute-5 alpha androstane derivatives and preparation method and application thereof | |
| CN106083963A (en) | A kind of preparation method of Suo Feibuwei crystal formation 6 | |
| CN105859810A (en) | Closed-ring byproduct I of 1-(2-deoxidatoin-beta-ribofuranose-based)-5-iodine-2-pyrmodone and preparing method of closed-ring byproduct I | |
| CN104130207B (en) | Acotiamide hydrobromide hydrate and the preparation method of crystal formation thereof | |
| CN106554339B (en) | A kind of isoflavone derivative and its preparation method and application | |
| CN106905236B (en) | Blonanserin and preparation method thereof | |
| CN105801643A (en) | Degradation product I of 1-(2-deoxy-beta-ribofuranose base)-5-iodine-2-pyrimidone and preparing method of degradation product I | |
| CN105175307A (en) | Lu AE58054 hydrochloride crystal form A, preparation method and uses thereof | |
| CN110204483A (en) | A kind of Sorafenib Tosylate novel crystal forms and preparation method thereof | |
| CN107721897A (en) | A kind of Levetiracetam novel crystal forms and preparation method thereof | |
| CN103709135B (en) | Ton ketone derivatives and its preparation method and application | |
| CN100506819C (en) | Heteraryl ring thiosemicarbazone kind compound and its derivative | |
| CN117355528B (en) | Salt type pyrrolotriazine compound, crystal form and preparation method thereof | |
| CN111138482B (en) | Tris (2-methyl-2-phenylpropyl) tin 5-bromo-2-furoate complex and preparation method and application thereof | |
| CN109400479B (en) | Bicyclic unsaturated ketone derivative with antibacterial and antitumor activities and preparation method thereof | |
| CN111138473B (en) | Tris (2-methyl-2-phenylpropyl) tin 3-methyl-thiophene-2-formate and preparation method and application thereof | |
| CN110869351B (en) | Crystalline forms of (R) -N- (4-chlorophenyl) -2- (cis-4- (6-fluoroquinolin-4-yl) cyclohexyl) propionamide | |
| CN104974200A (en) | Eutectic crystals of Helicid and L-proline and preparation method thereof | |
| CN112250657B (en) | Bicyclol dimer, preparation method and application thereof | |
| CN102690275A (en) | Tetrahydrofuro-[3,4-c]pyranyl-4-ketone compound and its preparation method and use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20160817 |