CN114736173B - Preparation method of 3- (difluoromethyl) oxetane-3-amine hydrochloride - Google Patents
Preparation method of 3- (difluoromethyl) oxetane-3-amine hydrochloride Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- FAZRGNCWSUTWGX-UHFFFAOYSA-N 3-(difluoromethyl)oxetan-3-amine hydrochloride Chemical compound C1C(CO1)(C(F)F)N.Cl FAZRGNCWSUTWGX-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 229940126214 compound 3 Drugs 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 21
- -1 t-butylsulfinyl group Chemical group 0.000 claims abstract description 21
- 230000008569 process Effects 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 229940125904 compound 1 Drugs 0.000 claims abstract description 10
- 229940125782 compound 2 Drugs 0.000 claims abstract description 10
- 229940125898 compound 5 Drugs 0.000 claims abstract description 9
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000009471 action Effects 0.000 claims abstract description 3
- 238000005869 desulfonation reaction Methods 0.000 claims abstract description 3
- 239000002994 raw material Substances 0.000 claims abstract description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- 229910004373 HOAc Inorganic materials 0.000 claims description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000012452 mother liquor Substances 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 230000003321 amplification Effects 0.000 abstract description 3
- 238000003199 nucleic acid amplification method Methods 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 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
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 150000002921 oxetanes Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VKUZMNXQGKBLHN-UHFFFAOYSA-N 2-methyl-n-(oxetan-3-ylidene)propane-2-sulfinamide Chemical compound CC(C)(C)S(=O)N=C1COC1 VKUZMNXQGKBLHN-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005842 biochemical reaction Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- LRHDNAVPELLXDL-UHFFFAOYSA-N difluoromethylsulfonylbenzene Chemical compound FC(F)S(=O)(=O)C1=CC=CC=C1 LRHDNAVPELLXDL-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002514 liquid chromatography mass spectrum Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Abstract
The invention discloses a preparation method of 3- (difluoromethyl) oxetane-3-amine hydrochloride, which comprises the following steps: (1) Compound 1 and compound 2 are used as initial raw materials, and compound 3 is synthesized under the action of LiHMDS/THF; (2) performing desulfonation reaction on the compound 3 to obtain a compound 4; (3) Compound 4 was subjected to t-butylsulfinyl group to give compound 5, the 3- (difluoromethyl) oxetan-3-amine hydrochloride. The method has the advantages of convenient operation, mild and easily controlled reaction conditions, lower cost, suitability for process amplification, easy purification of products and higher yield.
Description
Technical Field
The invention relates to the technical field of medical intermediates, in particular to a preparation method of 3- (difluoromethyl) oxetane-3-amine hydrochloride.
Background
In the recent development of chemical medicines and pesticides, heterocyclic compounds occupy an important position, and 90% of the world's new medicines are heterocyclic compounds. The oxetane is a four-membered ring ether compound, comprises types of monofunctional oxetane, difunctional oxetane, modified oxetane and the like, has ring tension smaller than that of a three-membered ring, but has high reactivity and easy ring opening to generate cationic activity because of strong alkalinity, namely strong nucleophilicity, can be used as an active diluent for reducing viscosity to be added into a cationic polymerization system to be used as a polymerization monomer for copolymerization with other compounds and the like.
The oxetane-based structure is subjected to chemical modification to obtain different functional groups and functionalities, so that the oxetane derivative is endowed with different performance characteristics and uses.
In addition, the oxygen atom of the oxetane is easy to generate coordination bonds by metal ions, so that the water solubility of the organic drug molecules can be improved, the four-ring structure of the oxetane is not easy to participate in biochemical reaction, the physicochemical characteristics of partially active carbonyl groups and the like of the drug can be replaced, and the thinking is developed for the design of the drug molecules.
At present, the synthesis of the 3- (difluoromethyl) oxetane-3-amine hydrochloride is not reported, so that it is significant to design a reasonable synthesis route.
Disclosure of Invention
The invention provides a preparation method of 3- (difluoromethyl) oxetane-3-amine hydrochloride, aiming at the problems existing in the prior art. The method has the advantages of convenient operation, mild and easily controlled reaction conditions, lower cost, suitability for process amplification, easy purification of products and higher yield.
The technical scheme of the invention is as follows:
a process for the preparation of 3- (difluoromethyl) oxetan-3-amine hydrochloride, said process comprising the steps of:
(1) Synthesizing N- (3- (difluoro (benzenesulfonyl) methyl) oxetan-3-yl) -2-methylpropan-2-sulfonamide (compound 3) by using 3- [ (tert-butylsulfinyl) imino ] oxetan (compound 1) and difluoromethyl phenyl sulfone (compound 2) as initial raw materials under the action of LiHMDS/THF;
(2) The compound 3 is subjected to desulfonation reaction to prepare N- (3- (difluoromethyl) oxetan-3-yl) -2-methylpropane-2-sulfonamide (compound 4);
(3) Compound 4 was subjected to t-butylsulfinyl group to give compound 5, the 3- (difluoromethyl) oxetan-3-amine hydrochloride.
In the step (1), the specific process is as follows: at room temperature, dissolving the compound 1 and the compound 2 in tetrahydrofuran, cooling to-40-78 ℃, dropwise adding 1-3 equivalents of LiHMDS/THF solution into the reaction liquid, reacting for 1-3 hours, adding water for quenching, extracting and concentrating by adopting ethyl acetate to obtain a crude product, and purifying the crude product by a column to obtain the compound 3. The molar ratio of the compound 1 to the compound 2 is 1:1-1:1.5.
In the step (2), the specific process is as follows: at room temperature, the compound 3 is dissolved in DMF, naOAc/HOAc solution is added, then 1-20 eq magnesium chips are slowly added in batches, the reaction is carried out for 2-24 hours at room temperature, filtration is carried out, saturated saline solution is added into the mother liquor, then MTBE (methyl tert-butyl ether) is used for extraction, and the organic phase is concentrated to obtain the compound 4. The concentration of NaOAc/HOAc solution is 1-10 mol/L, wherein the molar ratio of NaOAc to compound 3 is 1:1-1:40.
In the step (3), the specific process is as follows: at room temperature, the compound 4 is dissolved in dichloromethane, cooled to-5 ℃, HCl solution is added for reaction for 2 hours, MTBE is added into the reaction liquid, and the compound 5 is obtained by filtering, namely the 3- (difluoromethyl) oxetane-3-amine hydrochloride.
In the step (3), the HCl solution is one or more of HCl/MeOH, HCl/dioxane and HCl/Et 2 O. The molar ratio of HCl in the HCl solution to the compound 4 is 1:1-10:1.
The beneficial technical effects of the invention are as follows:
The synthesis method is reported for the first time, and the method has the advantages of convenient operation, mild and easily controlled reaction conditions, lower cost, suitability for process amplification, easy purification of products and higher yield.
Drawings
FIG. 1 is a schematic illustration of the reaction scheme of the present invention;
FIG. 2 is a LCMS spectrum of compound 3 prepared in example 1;
FIG. 3 is a nuclear magnetic resonance spectrum of the compound 3 prepared in example 1;
FIG. 4 is a nuclear magnetic resonance spectrum of the compound 4 prepared in example 1;
FIG. 5 is a nuclear magnetic resonance spectrum of the compound 5 prepared in example 1.
Detailed Description
The present invention will be described in detail below with reference to the drawings and examples.
Example 1
A process for the preparation of 3- (difluoromethyl) oxetan-3-amine hydrochloride, comprising the steps of:
(1) Preparation of N- (3- (difluoro (benzenesulfonyl) methyl) oxetan-3-yl) -2-methylpropan-2-sulfonamide (Compound 3)
Compound 1 (5 g,26 mmol) and compound 2 (4.6 g,26 mmol) were dissolved in tetrahydrofuran (100 mL) at room temperature, cooled to-78 ℃, liHMDS/THF (31 mL,1 mol/L) was slowly added dropwise to the reaction solution, reacted for 1h at-78 ℃, quenched with water, extracted 3 times with ethyl acetate, separated into organic phases, combined, washed with saturated brine, dried over sodium sulfate, filtered, concentrated to crude, and chromatographed with 200-300 mesh silica gel column to give 9g of off-white solid, compound 3, yield 94%, LCMS of which is shown in fig. 2, LCMS (m+1) +＝368.1,tR = 2.70min as seen in fig. 2; the nuclear magnetic hydrogen spectrum is shown in figure 3, and can be seen from figure 3 ,1H NMR(400MHz,DMSO-d6)δ8.05–7.90(m,3H),7.78(t,J＝7.8Hz,2H),6.43(s,1H),5.14–5.03(m,1H),4.98–4.81(m,3H),1.21(s,9H).
(2) Preparation of N- (3- (difluoromethyl) oxetan-3-yl) -2-methylpropan-2-sulfonamide (Compound 4)
Compound 3 (9 g,24.5 mmol) was dissolved in DMF (100 mL), 8mol/L NaOAc/HOAc solution (100 mL) was added, then magnesium turnings (11.9 g,0.49 mol) were slowly added in batches, reacted for 2H at room temperature, filtered, saturated saline was added to the mother liquor followed by 3 extractions with MTBE, the organic phases combined, dried over sodium sulfate, filtered and concentrated to give 4.7g of colorless oil, compound 4, yield 85%, whose nuclear magnetic hydrogen spectrum is shown in FIG. 4, 1H NMR(400MHz,DMSO-d6) delta 6.23 (t, J=55.4 Hz, 2H), 4.62 (d, J=11.2 Hz, 4H), 1.16 (s, 9H).
(3) Preparation of 3- (difluoromethyl) oxetan-3-amine hydrochloride (Compound 5)
Compound 4 (4.7 g,21 mmol) was dissolved in dichloromethane (50 mL) at room temperature, cooled to-5 ℃, HCl/dioxane (4 mol/L,10 mL) solution was added, the reaction was carried out for 2h at-5 ℃, MTBE was added to the reaction solution, and 3.1g of a white solid, namely 3- (difluoromethyl) oxetan-3-amine hydrochloride, was obtained by filtration in 94% yield.
Example 2
A process for the preparation of 3- (difluoromethyl) oxetan-3-amine hydrochloride, comprising the steps of:
(1) Preparation of N- (3- (difluoro (benzenesulfonyl) methyl) oxetan-3-yl) -2-methylpropan-2-sulfonamide (Compound 3)
Compound 1 (5 g,26 mmol) and Compound 2 (5.5 g,31 mmol) were dissolved in tetrahydrofuran (100 mL) at room temperature, cooled to-60℃and LiHMDS/THF (52 mL,1 mol/L) was slowly added dropwise to the reaction solution, reacted at-60℃for 2h, quenched with water, extracted 3 times with ethyl acetate, separated into organic phases, combined, washed with saturated brine, dried over sodium sulfate, filtered, concentrated to crude, chromatographed on a 200-300 mesh silica gel column to give 7.9g of an off-white solid, compound 3, yield 83%.
(2) Preparation of N- (3- (difluoromethyl) oxetan-3-yl) -2-methylpropan-2-sulfonamide (Compound)
Compound 3 (7.9 g,21.5 mmol) was dissolved in DMF (80 mL) at room temperature, 4mol/L NaOAc/HOAc solution (80 mL) was added, then magnesium turnings (5.2 g,0.215 mol) were slowly added in batches, reacted for 12h at room temperature, filtered, after adding saturated saline solution to the mother liquor, extracted 3 times with MTBE, the organic phases combined, dried over sodium sulfate, filtered and concentrated to give 3.4g of colorless oil, compound 4, yield 70%.
(3) Preparation of 3- (difluoromethyl) oxetan-3-amine hydrochloride (Compound 5)
Compound 4 (3.4 g,15 mmol) was dissolved in dichloromethane (35 mL) at room temperature, cooled to-5 ℃, HCl/MeOH (4 mol/L,18 mL) solution was added, reacted for 2h at-5 ℃, MTBE was added to the reaction solution, and filtered to give 2.1g of a white solid, namely the 3- (difluoromethyl) oxetan-3-amine hydrochloride, in a yield of 90%.
Example 3
A process for the preparation of 3- (difluoromethyl) oxetan-3-amine hydrochloride, comprising the steps of:
(1) Preparation of N- (3- (difluoro (benzenesulfonyl) methyl) oxetan-3-yl) -2-methylpropan-2-sulfonamide (Compound 3)
Compound 1 (5 g,26 mmol) and Compound 2 (6.8 g,39 mmol) were dissolved in tetrahydrofuran (100 mL) at room temperature, cooled to-40 ℃, liHMDS/THF (78 mL,1 mol/L) was slowly added dropwise to the reaction solution, the reaction was carried out at-40℃for 3h, quenched with water, extracted 3 times with ethyl acetate, separated into organic phases, the organic phases were combined, washed with saturated brine, dried over sodium sulfate, filtered, concentrated to crude, and chromatographed on a 200-300 mesh silica gel column to give 6.9g of an off-white solid, compound 3, yield 72%.
(2) Preparation of N- (3- (difluoromethyl) oxetan-3-yl) -2-methylpropan-2-sulfonamide (Compound 4)
Compound 3 (6.9 g,19 mmol) was dissolved in DMF (70 mL) at room temperature, 1mol/LNaOAc/HOAc solution (70 mL) was added, then magnesium turnings (2.3 g,94 mmol) were slowly added in batches, reacted for 24h at room temperature, filtered, saturated brine was added to the mother liquor and extracted 3 times with MTBE, the organic phases combined, dried over sodium sulfate, filtered and concentrated to give 2.3g of compound 4 as a colourless oil in 55% yield.
(3) Preparation of 3- (difluoromethyl) oxetan-3-amine hydrochloride (Compound 5)
Compound 4 (2.3 g,10 mmol) was dissolved in dichloromethane (25 mL) at room temperature, cooled to-5deg.C, HCl/Et 2 O (4 mol/L,20 mL) solution was added, reacted at-5deg.C for 2h, MTBE was added to the reaction solution, and filtered to give 1.4g of a white solid, namely the 3- (difluoromethyl) oxetan-3-amine hydrochloride, in 88% yield.
Claims (7)
1. A process for the preparation of 3- (difluoromethyl) oxetan-3-amine hydrochloride, said process comprising the steps of:
(1) Compound 1 and compound 2 are used as initial raw materials, and compound 3 is synthesized under the action of LiHMDS/THF;
(2) The compound 3 is subjected to a desulfonation reaction to prepare a compound 4;
(3) Removing tert-butylsulfinyl from the compound 4 to obtain a compound 5, namely 3- (difluoromethyl) oxetane-3-amine hydrochloride;
In the step (3), the specific process is as follows: at room temperature, the compound 4 is dissolved in dichloromethane, cooled to-5 ℃, HCl solution is added for reaction for 2 hours, MTBE is added into the reaction liquid, and the compound 5 is obtained by filtering, namely the 3- (difluoromethyl) oxetane-3-amine hydrochloride.
2. The preparation method according to claim 1, wherein in the step (1), the specific process is: at room temperature, dissolving the compound 1 and the compound 2 in tetrahydrofuran, cooling to-40 to-78 ℃, dropwise adding 1-3 equivalents of LiHMDS/THF solution into the reaction liquid, reacting for 1-3 hours, adding water for quenching, extracting and concentrating by adopting ethyl acetate to obtain a crude product, and purifying the crude product by a column to obtain the compound 3.
3. The preparation method according to claim 2, wherein the molar ratio of the compound 1 to the compound 2 is 1:1 to 1:1.5.
4. The preparation method according to claim 1, wherein in the step (2), the specific process is: at room temperature, the compound 3 is dissolved in DMF, naOAc/HOAc solution is added, then 1-20 eq magnesium chips are slowly added in batches, the reaction is carried out for 2-24 hours at room temperature, filtration is carried out, saturated saline solution is added into the mother liquor, then MTBE (methyl tert-butyl ether) is used for extraction, and the organic phase is concentrated to obtain the compound 4.
5. The method according to claim 4, wherein the concentration of NaOAc/HOAc solution is 1-10 mol/L, and the molar ratio of NaOAc to compound 3 is 1:1-1:40.
6. The process of claim 1, wherein in step (3), the HCl solution is one or more of HCl/MeOH, HCl/dioxane, HCl/Et 2 O.
7. The preparation method according to claim 1, wherein the molar ratio of HCl to compound 4 in the HCl solution is 1:1 to 10:1.
Priority Applications (1)
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| CN202210568126.3A CN114736173B (en) | 2022-05-24 | Preparation method of 3- (difluoromethyl) oxetane-3-amine hydrochloride |
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| CN202210568126.3A CN114736173B (en) | 2022-05-24 | Preparation method of 3- (difluoromethyl) oxetane-3-amine hydrochloride |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102596913A (en) * | 2009-08-28 | 2012-07-18 | 艾尼纳制药公司 | Cannabinoid receptor modulators |
| CN107108643A (en) * | 2014-12-23 | 2017-08-29 | 吉利德科学公司 | Polycyclic carbonic acyl radical pyridinone compounds and its medicinal usage |
| WO2021155316A1 (en) * | 2020-01-29 | 2021-08-05 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| CN114072390A (en) * | 2019-03-12 | 2022-02-18 | 赛泰尔治疗公司 | RAD51 inhibitors |
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102596913A (en) * | 2009-08-28 | 2012-07-18 | 艾尼纳制药公司 | Cannabinoid receptor modulators |
| CN107108643A (en) * | 2014-12-23 | 2017-08-29 | 吉利德科学公司 | Polycyclic carbonic acyl radical pyridinone compounds and its medicinal usage |
| CN114072390A (en) * | 2019-03-12 | 2022-02-18 | 赛泰尔治疗公司 | RAD51 inhibitors |
| WO2021155316A1 (en) * | 2020-01-29 | 2021-08-05 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
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