CN115925559A - Preparation method of 1-amino-1-cyclopentyl methanol - Google Patents
Preparation method of 1-amino-1-cyclopentyl methanol Download PDFInfo
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- CN115925559A CN115925559A CN202211412291.6A CN202211412291A CN115925559A CN 115925559 A CN115925559 A CN 115925559A CN 202211412291 A CN202211412291 A CN 202211412291A CN 115925559 A CN115925559 A CN 115925559A
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- AXNJKYLFCKEIHI-UHFFFAOYSA-N amino(cyclopentyl)methanol Chemical compound NC(O)C1CCCC1 AXNJKYLFCKEIHI-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 22
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000010992 reflux Methods 0.000 claims abstract description 17
- NILQLFBWTXNUOE-UHFFFAOYSA-N 1-aminocyclopentanecarboxylic acid Chemical compound OC(=O)C1(N)CCCC1 NILQLFBWTXNUOE-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 14
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 14
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011630 iodine Substances 0.000 claims abstract description 12
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 239000000047 product Substances 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 13
- 238000010791 quenching Methods 0.000 claims description 13
- 238000001035 drying Methods 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 230000000171 quenching effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000009776 industrial production Methods 0.000 abstract description 5
- 150000003839 salts Chemical class 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 8
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 7
- -1 cycloalkyl oxazoline Chemical compound 0.000 description 7
- 238000001514 detection method Methods 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 239000007810 chemical reaction solvent Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- AZHSSKPUVBVXLK-UHFFFAOYSA-N ethane-1,1-diol Chemical compound CC(O)O AZHSSKPUVBVXLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
The invention provides a preparation method of 1-amino-1-cyclopentyl methanol, which comprises the following steps: mixing and reacting cycloleucine, sodium borohydride, iodine and tetrahydrofuran, desolventizing after the reaction is finished, mixing and refluxing with palladium-carbon, and performing post-treatment to obtain the 1-amino-1-cyclopentyl methanol. The preparation method provided by the invention has the advantages of mild reaction conditions, high yield, simple post-treatment and high product purity, and is suitable for industrial production.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of 1-amino-1-cyclopentyl methanol, in particular to a preparation method of high-purity 1-amino-1-cyclopentyl methanol.
Background
1-amino-1-cyclopentyl methanol plays an important role in a variety of commercial and consumer products; the compound is used as a key organic synthesis intermediate for researching and developing new drugs and special chemical product intermediates, and can also be used for preparing amino acid and other bioactive compounds and material additives. The 1-amino-1-cyclopentyl methanol is also commonly used for preparing a levelling agent, can be suitable for dyeing wool, silk and nylon by acid dyes, and has important effects on improving the product quality of a printing and dyeing mill and preventing dyeing defects.
CN104926747B discloses a synthesis method of cycloalkyl oxazoline ligand with optical activity and its use. The method for preparing 1-amino-1-cyclopentyl methanol by adopting the reaction of cycloleucine and lithium aluminum hydride is disclosed, however, the lithium aluminum hydride has high reaction activity and great danger and is not suitable for industrial production, and meanwhile, the reaction post-treatment of the lithium aluminum hydride is complex and the product purity is not high.
Therefore, how to provide a preparation method of 1-amino-1-cyclopentyl methanol with high purity and good yield becomes a problem to be solved urgently.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a preparation method of 1-amino-1-cyclopentyl methanol, in particular to a preparation method of 1-amino-1-cyclopentyl methanol with high purity. The preparation method provided by the invention has the advantages of mild reaction conditions, high yield, simple post-treatment and high product purity, and is suitable for industrial production.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a preparation method of 1-amino-1-cyclopentyl methanol, which comprises the following steps:
mixing and reacting cycloleucine, sodium borohydride, iodine and tetrahydrofuran, desolventizing after the reaction is finished, mixing and refluxing with palladium-carbon, and performing post-treatment to obtain the 1-amino-1-cyclopentyl methanol.
According to the method, sodium borohydride is used for replacing lithium aluminum hydride in the conventional method, so that the requirement on reaction conditions can be effectively reduced, and the reaction solvent is removed and then the reaction solvent and palladium carbon are subjected to reflux reaction after the reaction is finished, so that the addition amount of the palladium carbon can be effectively reduced, and a large amount of raw materials and cost are saved; meanwhile, the post-treatment is simple, the yield is high, the product purity is high, and the method is suitable for industrial production.
Preferably, the molar ratio of the cycloleucine to the sodium borohydride to the iodine is 1 (4-8) to (2.5-3.5).
Preferably, the reaction temperature is 20-30 ℃ and the reaction time is 20-28h.
Wherein, the molar ratio of cycloleucine, sodium borohydride and iodine can be 1.
Preferably, a quenching agent is added after the reaction is finished to quench the reaction, wherein the quenching agent comprises alcohol, and the alcohol comprises methanol and/or ethanol.
Preferably, the refluxing is carried out in a solvent comprising an alcohol comprising methanol and/or ethanol.
Preferably, the alcohol is methanol.
The specific alcohol can effectively dissolve reaction raw materials and products, improve the speed of the subsequent treatment process and shorten the treatment time.
Preferably, the mass ratio of the cycloleucine to the palladium carbon is 1 (0.05-0.1), and the mass fraction of the palladium carbon is 5-15%.
Preferably, the refluxing time is 40-50h.
The mass ratio of cyclic leucine to palladium carbon may be 1.05, 1.
Preferably, the post-treatment comprises the steps of: and filtering and spin-drying the refluxed product, dissolving the spin-dried product with a solvent, filtering, and spin-drying the filtrate again to obtain the 1-amino-1-cyclopentyl methanol.
Preferably, the solvent comprises dichloromethane and/or ethyl acetate.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a preparation method of 1-amino-1-cyclopentyl methanol, which can effectively reduce the requirement of reaction conditions by adopting sodium borohydride to replace lithium aluminum hydride in the conventional method, and can effectively reduce the addition amount of palladium-carbon and save a large amount of raw materials and cost by removing the reaction solvent and then carrying out reflux reaction with the palladium-carbon after the reaction is finished; meanwhile, the post-treatment is simple, the yield is high, the product purity is high, and the method is suitable for industrial production.
Detailed Description
In order to further illustrate the technical means and effects of the present invention, the technical solutions of the present invention are further described below with reference to the preferred embodiments of the present invention, but the present invention is not limited to the scope of the embodiments.
Example 1
The embodiment provides a preparation method of 1-amino-1-cyclopentyl methanol, which comprises the following specific steps:
cycloleucine (148 g) and sodium borohydride (260 g) are dissolved in tetrahydrofuran (2500 mL), iodine (872.6 g) is added to the system slowly in portions under ice bath conditions, and the mixture is stirred for 24h at 25 ℃. TLC points on the plate, ninhydrin color development confirms the reaction is completed, then methanol is added under ice bath to quench the reaction, spin drying is carried out, methanol is added to dissolve, 10.4g Pd/C (10%) is added to reflux for 48h, then Pd/C is filtered and removed, spin drying is carried out, dichloromethane is used for dissolving, salt is separated out, clear and transparent filtrate can be obtained after the salt is filtered and removed, and spin drying is carried out to obtain 95g of product, the yield is 72%, and the purity is 98% (GCMS detection). The characterization data are as follows: 1 H NMR(400MHz,dmso)δ3.20(d,J＝17.4Hz 2H),1.73-1.26(m 8H)。
example 2
The embodiment provides a preparation method of 1-amino-1-cyclopentyl methanol, which comprises the following specific steps:
cycloleucine (148 g) and sodium borohydride (174 g) are dissolved in 2500mL of tetrahydrofuran, iodine (730 g) is added to the system slowly in portions under ice bath conditions, and the mixture is stirred for 28h at 20 ℃. And (3) performing TLC (thin layer chromatography) plate counting, confirming that the reaction is finished by ninhydrin color development, then adding ethanol alcohol under an ice bath to quench the reaction, spin-drying, adding ethanol to dissolve, adding 7.4g of Pd/C (10%) to reflux for 50h, then filtering to remove Pd/C, spin-drying, dissolving by ethyl acetate, precipitating salt, filtering to remove salt to obtain clear and transparent filtrate, and spin-drying to obtain a product 93.3g, wherein the yield is 70% and the purity is 97% (GCMS detection).
Example 3
The embodiment provides a preparation method of 1-amino-1-cyclopentyl methanol, which comprises the following specific steps:
cycloleucine (148 g) and sodium borohydride (348 g) are dissolved in 3000mL of tetrahydrofuran, iodine (1022 g) is added to the system slowly in portions under ice bath conditions, and the mixture is stirred for 20h at 30 ℃. TLC points on the plate, ninhydrin color development confirms the reaction is completed, methanol is added under ice bath to quench the reaction, the reaction is dried by spinning, methanol is added to dissolve the reaction, 14.8g Pd/C (10%) is added to reflux for 40h, then the Pd/C is filtered and removed, the reaction is dried by spinning, the reaction is dissolved by dichloromethane, salt is separated out, clear and transparent filtrate can be obtained after the salt is filtered and removed, and the product is dried by spinning, 94.6g is obtained, the yield is 71%, and the purity is 97% (GCMS detection).
Example 4
The embodiment provides a preparation method of 1-amino-1-cyclopentyl methanol, which comprises the following specific steps:
cycloleucine (148 g) and sodium borohydride (260 g) were dissolved in 2500mL of tetrahydrofuran, and iodine (872.6 g) was added to the system in portions slowly under ice bath conditions, followed by stirring at 25 ℃ for 24 hours. TLC points on the plate, ninhydrin color development confirms the reaction is completed, then methanol is added under ice bath to quench the reaction, spin-dry, methanol is added to dissolve, 88.8g Pd/C (10%) is added to reflux for 48h, then Pd/C is filtered and removed, spin-dry, and dissolved by dichloromethane, salt can be separated out, clear transparent filtrate can be obtained after salt is filtered and removed, and spin-dry is carried out to obtain 96.3g of product, yield is 73%, and purity is 98% (GCMS detection). The characterization data are as follows: 1 H NMR(400MHz,dmso)δ3.20(d,J＝17.4Hz 2H),1.73-1.26(m 8H)。
comparative example 1
The comparative example provides a preparation method of 1-amino-1-cyclopentyl methanol, which comprises the following specific steps:
cycloleucine (148 g) and sodium borohydride (260 g) are dissolved in tetrahydrofuran (2500 mL), iodine (872.6 g) is added to the system slowly in portions under ice bath conditions, and the mixture is stirred for 24h at 25 ℃. TLC point plate, ninhydrin color development confirm reaction completion, then add methanol under ice bath quench reaction, then add 10.4g Pd/C (10%) reflux 48h, then filter to remove Pd/C, spin dry, and dissolve with dichloromethane, salt will precipitate, filter to remove salt to obtain product 99g, yield 63.5%, purity 83% (GCMS detection).
Comparative example 2
The comparative example provides a preparation method of 1-amino-1-cyclopentyl methanol, which comprises the following specific steps:
cycloleucine (148 g) and sodium borohydride (260 g) were dissolved in 2500mL of tetrahydrofuran, and iodine (872.6 g) was added to the system in portions slowly under ice bath conditions, followed by stirring at 25 ℃ for 24 hours. The TLC plate is checked, ninhydrin color is shown to confirm the reaction is finished, then methanol is added under ice bath to quench the reaction, then 88.8g Pd/C (10%) is added for refluxing for 48h, then Pd/C is removed by filtration, spin-drying is carried out, methylene chloride is used for dissolution, salt is separated out, and the product 105.4g is obtained by filtering and removing salt, the yield is 66%, and the purity is 81% (GCMS detection).
Comparative example 3
The comparative example provides a preparation method of 1-amino-1-cyclopentyl methanol, which comprises the following specific steps:
cycloleucine (4 g) was dissolved in 50mL of tetrahydrofuran, and lithium aluminum hydride (2.4 g) was added to the system slowly in portions under ice salt bath conditions, followed by stirring at 0 ℃ for 1h. TLC point plate, ninhydrin color development confirm reaction completion, then add sodium sulfate decahydrate under ice bath quench reaction, add after stirring for one hour, suction filtration, filter cake with tetrahydrofuran washing, filtrate evaporation to dryness to obtain 2.73g brown oil product, yield 55.2%, purity 72% (GCMS detection).
The results show that the preparation method provided by the invention can be used for simply and efficiently synthesizing and preparing the 1-amino-1-cyclopentyl methanol; comparing example 1 with comparative examples 1-2, it can be found that example 1 can effectively reduce the amount of palladium carbon added and save a lot of raw materials and cost by removing the reaction solvent after the reaction is finished and then refluxing with palladium carbon, and the similar effect can be barely achieved by adding more palladium carbon without removing the reaction solvent and directly adding palladium carbon to carry out refluxing; comparing example 1 with comparative example 3, it can be seen that the invention not only has milder reaction conditions, safer reaction, but also has higher product purity compared with the conventional method; comparing examples 1 and 4, it can be seen that although the yield can be improved by increasing the amount of palladium carbon, the increased amount is smaller, and a large amount of palladium carbon needs to be added, so that the cost is higher, while the preparation of high-yield and high-purity 1-amino-1-cyclopentyl methanol can be realized by only a small amount of palladium carbon in example 1, so that the cost is significantly reduced.
The applicant states that the present invention is illustrated by the above examples for the preparation of 1-amino-1-cyclopentyl methanol according to the present invention, but the present invention is not limited to the above examples, i.e. it is not meant to be construed as being limited to the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition.
Claims (10)
1. A preparation method of 1-amino-1-cyclopentyl methanol is characterized by comprising the following steps:
mixing and reacting cycloleucine, sodium borohydride, iodine and tetrahydrofuran, desolventizing after the reaction is finished, mixing and refluxing with palladium-carbon, and performing post-treatment to obtain the 1-amino-1-cyclopentyl methanol.
2. The method of claim 1, wherein the molar ratio of cycloleucine, sodium borohydride and iodine is 1 (4-8) to (2.5-3.5).
3. The process according to claim 1 or 2, wherein the reaction is carried out at a temperature of 20 to 30 ℃ for a time of 20 to 28 hours.
4. The method according to any one of claims 1 to 3, wherein a quenching agent is added after the reaction is completed to quench the reaction, wherein the quenching agent comprises an alcohol, and the alcohol comprises methanol and/or ethanol.
5. The method according to any one of claims 1 to 4, wherein the refluxing is carried out in a solvent comprising an alcohol comprising methanol and/or ethanol.
6. The method according to claim 5, wherein the alcohol is methanol.
7. The production method according to any one of claims 1 to 6, wherein the mass ratio of the cycloleucine to the palladium on carbon is 1 (0.05-0.1), and the mass fraction of the palladium on carbon is 5-15%.
8. The method according to any one of claims 1 to 7, wherein the reflux time is 40 to 50 hours.
9. The method for preparing according to any one of claims 1 to 8, wherein the post-treatment comprises the steps of: and filtering and spin-drying the refluxed product, dissolving the spin-dried product with a solvent, filtering, and spin-drying the filtrate again to obtain the 1-amino-1-cyclopentyl methanol.
10. The method of claim 9, wherein the solvent comprises dichloromethane and/or ethyl acetate.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1337955A (en) * | 1999-01-14 | 2002-02-27 | 美国拜尔公司 | Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents |
| CN101874015A (en) * | 2007-09-28 | 2010-10-27 | 弗吉尼亚大学专利基金会 | Benzyl-cycloalkyl sphingosine 1-phosphate receptor modulators |
| US20170333440A1 (en) * | 2014-04-17 | 2017-11-23 | G1 Therapeutics, Inc. | Tricyclic lactams for use in hspc-sparing treatments for rb-positive abnormal cellular proliferation |
-
2022
- 2022-11-11 CN CN202211412291.6A patent/CN115925559A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1337955A (en) * | 1999-01-14 | 2002-02-27 | 美国拜尔公司 | Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents |
| CN101874015A (en) * | 2007-09-28 | 2010-10-27 | 弗吉尼亚大学专利基金会 | Benzyl-cycloalkyl sphingosine 1-phosphate receptor modulators |
| US20170333440A1 (en) * | 2014-04-17 | 2017-11-23 | G1 Therapeutics, Inc. | Tricyclic lactams for use in hspc-sparing treatments for rb-positive abnormal cellular proliferation |
Non-Patent Citations (1)
| Title |
|---|
| MIN ZHU等: "Synthesis of NH-Aziridines from Vicinal Amino Alcohols Via the Wenker Reaction: Scope and Limitation", LETTERS IN ORGANIC CHEMISTRY, vol. 5, no. 3, 31 December 2008 (2008-12-31), pages 212 - 217 * |
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