CN119143732A - Preparation method of lenalidomide impurity A - Google Patents
Preparation method of lenalidomide impurity A Download PDFInfo
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- CN119143732A CN119143732A CN202411605130.8A CN202411605130A CN119143732A CN 119143732 A CN119143732 A CN 119143732A CN 202411605130 A CN202411605130 A CN 202411605130A CN 119143732 A CN119143732 A CN 119143732A
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- Prior art keywords
- lenalidomide
- compound
- preparation
- impurity
- solvent
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- GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 229960004942 lenalidomide Drugs 0.000 title claims abstract description 49
- 239000012535 impurity Substances 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229940125782 compound 2 Drugs 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 13
- 229940125904 compound 1 Drugs 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- FCGIVHSBEKGQMZ-UHFFFAOYSA-N methyl 2-(bromomethyl)-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1CBr FCGIVHSBEKGQMZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002841 Lewis acid Substances 0.000 claims abstract description 7
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 7
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 4
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 235000011181 potassium carbonates Nutrition 0.000 claims description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005695 Ammonium acetate Substances 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 235000019257 ammonium acetate Nutrition 0.000 claims description 2
- 229940043376 ammonium acetate Drugs 0.000 claims description 2
- 235000011167 hydrochloric acid Nutrition 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 3
- 239000002585 base Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 abstract description 6
- 229940079593 drug Drugs 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000013558 reference substance Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- 201000003793 Myelodysplastic syndrome Diseases 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to the technical field of drug impurity synthesis, in particular to a preparation method of lenalidomide impurity A, which comprises the following steps: (1) Heating lenalidomide and a compound 1 in a base and solvent system to perform cyclization reaction, and purifying by a column to obtain a compound 2, wherein the compound 1 is 2-bromomethyl-3-nitrobenzoic acid methyl ester; (2) The compound 2 is reduced by an inorganic metal reducing agent and a Lewis acid system in an alcohol solvent and water system, and is concentrated, crystallized, filtered and dried to prepare the lenalidomide impurity A, the invention provides a simple and high-efficiency directional synthesis method of the lenalidomide impurity A, and the cost is low, the method is mild in condition, only uses lenalidomide and compound 1 (lenalidomide intermediate, 2-bromomethyl-3-nitrobenzoic acid methyl ester) to be reduced after cyclization, and the lenalidomide impurity A prepared by the method is high in purity and can be used as an impurity reference substance for the quality study of lenalidomide.
Description
Technical Field
The invention relates to the technical field of drug impurity synthesis, in particular to a preparation method of lenalidomide impurity A.
Background
Lenalidomide (lenalidomide) is an anti-tumor and anti-tumor cell proliferation immunomodulating agent, can be used for treating multiple myeloma, mantle cell lymphoma and myelodysplastic syndrome, has the chemical name of 3- (4-amino-1-oxo-1, 3-dihydro-2H-isoindol-2-yl) piperidine-2, 6-dione, and has the chemical structure shown as follows:
the lenalidomide impurity A is one of important process impurities generated in the process of producing lenalidomide, plays an important role in controlling the quality of medicines of the lenalidomide, and is an important work in the process of developing medicines. The invention provides a method for directionally synthesizing lenalidomide impurity A, which is efficient and convenient, and the chemical structural formula of the lenalidomide impurity A is shown as follows:
Disclosure of Invention
The invention aims to provide a preparation method of lenalidomide impurity A.
The invention discloses a preparation method of lenalidomide impurity A, which comprises the following steps:
(1) Heating lenalidomide and compound 1 (2-bromomethyl-3-nitrobenzoic acid methyl ester) in a certain alkali/solvent system to carry out cyclization reaction, and purifying by a column to obtain a compound 2;
(2) Reducing the compound 2 in an alcohol solvent/water system by an inorganic metal reducing agent/Lewis acid system, concentrating, crystallizing, filtering and drying to obtain lenalidomide impurity A.
Preferably, the solvent in the step (1) is one or a combination of several of acetone, acetonitrile, tetrahydrofuran, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide and N-methylpyrrolidone.
It is further preferable that the solvent used in the step (1) is one selected from the group consisting of N, N-dimethylacetamide and N-methylpyrrolidone.
Preferably, the alkali in the step (1) is one or a combination of several of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, triethylamine, diisopropylethylamine and tributylamine.
Preferably, in the method of step (1), the molar feed ratio of the compound 1 to lenalidomide is 1-2:1.
Preferably, in the method of step (1), the reaction temperature is 50-80 ℃.
Preferably, the alcohol solvent used in the step (2) is selected from one or a combination of several of methanol, ethanol, isopropanol, n-butanol, 2-butanol and n-propanol.
Further preferably, the solvent used in the step (2) is selected from one of methanol and ethanol.
Preferably, the inorganic metal reducing agent used in the step (2) is one of reduced iron powder and zinc powder, and the lewis acid is one of ammonium chloride, hydrochloric acid, acetic acid, ammonium acetate and ammonium sulfate.
Preferably, in the method described in the step (2), the molar feed ratio of the inorganic metal reducing agent to the compound 2 is 2-6:1, and the molar feed ratio of the lewis acid to the compound 2 is 1-6:1.
Preferably, in the method of step (2), the reaction temperature is 70-90 ℃.
The invention provides a simple and efficient directional synthesis method of lenalidomide impurity A, which is low in cost and mild in condition, and is prepared by only using the cyclization of lenalidomide and a compound 1 (lenalidomide intermediate, 2-bromomethyl-3-nitrobenzoic acid methyl ester) and then reducing the compound, and the lenalidomide impurity A prepared by the method is high in purity and can be used as an impurity reference substance for the quality study of the lenalidomide.
Drawings
FIG. 1 is a 1 H-NMR spectrum of lenalidomide impurity A;
FIG. 2 is a 13 C-NMR chart of lenalidomide impurity A;
FIG. 3 is an MS detection pattern of lenalidomide impurity A.
Detailed Description
The invention is further illustrated and described below in connection with specific examples.
The invention discloses a preparation method of lenalidomide impurity A, which adopts the following synthetic route:
Example 1
The synthesis method of the compound 2 comprises the steps of sequentially adding 10g of lenalidomide (38.6 mmol), 10.6g of compound 1 (2-bromomethyl-3-nitrobenzoic acid methyl ester) (38.6 mmol), 300mL of acetonitrile and 9g of sodium bicarbonate (107 mmol) into a 500mL three-port bottle, heating to 80 ℃ for reaction for 48 hours, evaporating the solvent, directly purifying the residue by a column, and purifying by the column by using methanol/dichloromethane as an eluent to obtain 9.5g of white solid which is the compound 2 with the purity of >98 percent and the yield of 59 percent.
Example 2
The synthesis method of the compound 2 comprises the steps of sequentially adding 10g of lenalidomide (38.6 mmol), 14g of compound 1 (2-bromomethyl-3-nitrobenzoic acid methyl ester) (50 mmol), 100mL of N-methylpyrrolidone and 7.8g of triethylamine (77.2 mmol) into a 250mL three-port bottle, heating to 50 ℃ for 48 hours, evaporating the solvent, directly purifying the residue by a column, and purifying by the column by using methanol/dichloromethane as an eluent to obtain 12.7g of white solid, namely the compound 2 with the purity of >98% and the yield of 79%.
Example 3
The synthesis method of the compound 2 comprises the steps of sequentially adding 5g of lenalidomide (19.3 mmol), 10.6g of compound 1 (2-bromomethyl-3-nitrobenzoic acid methyl ester) (38.6 mmol), 50mlNN g of dimethylacetamide and 4.0g of potassium carbonate (29 mmol) into a 200mL three-port bottle, heating to 60 ℃ for reaction for 36 hours, evaporating the solvent, directly purifying the residue by a column, and purifying by the column by using methanol/dichloromethane as an eluent to obtain 7.1g of white solid, namely the compound 2, wherein the purity is more than 98%, and the yield is 88%.
Example 4
The synthesis method of the compound 2 comprises the steps of sequentially adding 10g of lenalidomide (38.6 mmol), 14g of compound 1 (2-bromomethyl-3-nitrobenzoic acid methyl ester) (50 mmol), 300mL of acetonitrile and 9g of triethylamine (107 mmol) into a 200mL three-port bottle, heating to 75 ℃ to react for 48 hours, evaporating the solvent, directly purifying the residue through a column, and purifying the residue through the column by using methanol/dichloromethane as an eluent to obtain 9.1g of white solid, namely the compound 2 with the purity of >98 percent and the yield of 56 percent.
Example 5
The preparation method of lenalidomide impurity A comprises the steps of adding 4.2g of compound 2 (10 mmol), 3.2g of ammonium chloride (60 mmol), 100ml of ethanol and 20ml of water into a 250ml three-port bottle in sequence, stirring, adding 2.3g (41 mmol) of reducing iron powder, heating to 75 ℃ for reaction for 2 hours, filtering, concentrating filtrate to remove most of solvent, adding 30ml of water, stirring, filtering, and drying to obtain 3.0g of light yellow solid, namely lenalidomide A with purity of >98% and yield of 77%, wherein the data of 1H-NMR、13 C-NMR and MS (APCI) of the lenalidomide A refer to figures 1-3 are as follows:
1H-NMR（500MHz,DMSO-d6）：δ10.98（s,1H）;δ7.82（d,J=7.75Hz,1H）;δ7.71（d, J=7.3Hz, 1H）;δ7.62-7.66（m,1H）;δ7.22-7.26（m,1H）;δ6.98（d, J=7.35Hz, 1H）;δ6.85（d, J=7.9Hz, 1H）;δ5.55（s,2H）; δ5.12-5.17（m,1H）; δ4.85（d, J=16.8Hz, 1H）; δ4.75（d, J=16.8Hz, 1H）; δ4.44-4.54（m,2H）; δ2.86-2.94（m,1H）; δ2.55-2.59（m,1H）; δ2.36-2.45（m,1H）; δ1.96 -1.99（m,1H）.
13C-NMR（125MHz,DMSO-d6）：δ172.81,170.87,167.53,166.85,143.61,137.03,134.59,133.22,131.97,129.06,128.99,127.74,125.86,121.02,116.51,110.59,51.49,50.40,47.20,31.15,22.41.
MS(APCI):391.7(M+H)。
Example 6
The preparation method of lenalidomide impurity A comprises the steps of adding 4.2g of compound 2 (10 mmol), 0.54g of ammonium chloride (10 mmol), 100ml of ethanol and 20ml of water into a 250ml three-port bottle in sequence, stirring, adding 1.3g of zinc powder (20 mmol), heating to 80 ℃ for reaction for 2 hours, filtering, concentrating filtrate to remove most of solvent, adding 30ml of water, stirring, filtering, and drying to obtain 2.6g of light yellow solid, namely lenalidomide impurity A, wherein the purity is more than 98%, and the yield is 67%.
Example 7
The preparation method of lenalidomide impurity A comprises the steps of adding 4.2g of compound 2 (10 mmol), 2.0g of ammonium sulfate (15.1 mmol), 100ml of ethanol and 20ml of water into a 250ml three-port bottle in sequence, stirring, adding 1.3g of zinc powder (20 mmol), heating to 70 ℃ for reaction for 2 hours, filtering, concentrating filtrate to remove most of solvent, adding 30ml of water, stirring, filtering, and drying to obtain 2.3g of light yellow solid which is lenalidomide impurity A, wherein the purity is more than 98%, and the yield is 59%.
Example 8
The preparation method of lenalidomide impurity A comprises the steps of adding 4.2g of compound 2 (10 mmol), 2.0g of ammonium sulfate (15.1 mmol), 60ml of n-butanol and 20ml of water into a 250ml three-port bottle in sequence, stirring, adding 3.4g (60 mmol) of reducing iron powder, heating to 90 ℃ for reaction for 4 hours, filtering, separating filtrate, separating organic phase, directly concentrating the organic phase, evaporating solvent to obtain 2.7g of yellow solid, namely lenalidomide impurity A, wherein the purity is more than 98%, and the yield is 69%.
The foregoing is merely exemplary of the present invention and is not intended to limit the present invention. Various modifications and variations of the present invention will be apparent to those skilled in the art. Any modification, equivalent replacement, improvement, etc. which come within the spirit and principles of the invention are to be included in the scope of the claims of the present invention.
Claims (10)
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| CN202411605130.8A CN119143732A (en) | 2024-11-12 | 2024-11-12 | Preparation method of lenalidomide impurity A |
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| CN202411605130.8A CN119143732A (en) | 2024-11-12 | 2024-11-12 | Preparation method of lenalidomide impurity A |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110021567A1 (en) * | 2008-03-11 | 2011-01-27 | Dr. Reddy's Laboratories Ltd. | Preparation of lenalidomide |
| CN113956189A (en) * | 2021-11-08 | 2022-01-21 | 深圳菲斯生物科技有限公司 | Preparation method of lenalidomide impurity D |
-
2024
- 2024-11-12 CN CN202411605130.8A patent/CN119143732A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110021567A1 (en) * | 2008-03-11 | 2011-01-27 | Dr. Reddy's Laboratories Ltd. | Preparation of lenalidomide |
| CN113956189A (en) * | 2021-11-08 | 2022-01-21 | 深圳菲斯生物科技有限公司 | Preparation method of lenalidomide impurity D |
Non-Patent Citations (1)
| Title |
|---|
| PING LU ET AL.: "Identification and characterization of related substances in pomalidomide by hyphenated LC–MS techniques", 《JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS》, vol. 114, 22 May 2015 (2015-05-22), pages 159 - 167, XP029260153, DOI: 10.1016/j.jpba.2015.05.018 * |
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