CN114246869A - Anti-tumor activity and application of bifeprunox and derivatives thereof - Google Patents
Anti-tumor activity and application of bifeprunox and derivatives thereof Download PDFInfo
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- CN114246869A CN114246869A CN202210052189.3A CN202210052189A CN114246869A CN 114246869 A CN114246869 A CN 114246869A CN 202210052189 A CN202210052189 A CN 202210052189A CN 114246869 A CN114246869 A CN 114246869A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Abstract
The invention provides application of bifeprunox or a derivative thereof and a pharmaceutical composition containing bifeprunox or a derivative thereof in preparing a medicament for preventing and/or treating tumors. Experiments show that the compound has obvious growth inhibition effect on various human tumor cells, has broad-spectrum anti-tumor activity, and has good inhibition activity on tumors such as breast cancer, esophageal cancer, thyroid cancer, nasopharyngeal cancer, cervical cancer, glioma, prostatic cancer, ovarian cancer, lung cancer, colorectal cancer, liver cancer, gastric cancer, melanoma, pancreatic cancer, leukemia, lymphoma and the like, and experiments show that the bifeprunox and derivatives thereof can become anti-tumor drugs.
Description
Technical Field
The invention relates to the technical field of medicines, in particular to application of bifeprunox and derivatives thereof in preparation of antitumor medicines.
Background
The English name of Bifeprunox is Bifepunox, and the chemical name is 7- [4- ([1,1' -biphenyl)]-3-ylmethyl) -1-piperazinyl]-2(3H) -benzoxazolone with the chemical name 7- [4- ([1,1' -Biphenyl)]-3-ylmethyl)-1-piperazinyl]-2(3H) -benzoxazone; the english name is Bifeprunox. The molecular formula of the compound is C24H23N3O2Molecular weight 385.46, dissolved in DMSO. Bifenapino belongs to a novel atypical antipsychotic drug, has atypical characteristics in the atypical antipsychotic drug, and has positive symptoms, negative symptoms and cognitive function on schizophreniaHas good curative effect on symptoms and emotional symptoms.
Disclosure of Invention
The invention adopts the following technical scheme:
the invention provides an application of bifeprunox or a derivative thereof or a pharmaceutical composition containing bifeprunox or a derivative thereof in preparing a medicament for preventing and/or treating tumors, wherein the bifeprunox is shown as a chemical structural formula (I):
（Ⅰ）
the bifeprunox derivative is shown as a chemical structural formula (II):
（П）
R1-R18each independently selected from hydrogen, hydroxy, amino, C1-8Alkyl radical, C1-8Alkoxy radical, C1-8Alcoxyl acyl radical, C2-8Alkenyl radical, C2-8Alkynyl, C1-8Acyl radical, C6-10Aryl radical, C5-6Cycloalkyl, tetrahydropyrroloyl, tetrahydrofuroyl, Ar-C1-4Acyl, Ar-O-C1-4Acyl, Ar-S-C1-4Any one or more of acyl; or R3And R4Or R9And R10Or R14And R15Linked to form a saturated or unsaturated 6-membered carbocyclic or heterocyclic group or an alkyl-substituted carbocyclic or heterocyclic group;
further, C1-8The acyl group is selected from the group consisting of straight or branched alkanoyl, alkenoyl and alkynoyl;
further, Ar is aryl or substituted aryl, Ar is preferably any one or more of phenyl, benzoyl, naphthyl, pyridyl, furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, pyridazinyl, pyrazinyl, benzofuryl, benzothienyl, indolyl, quinolyl, isoquinolyl, purinyl, benzoxazolyl and benzothiazolyl;
further, the bifeprunox or its derivative includes, but is not limited to, its tautomer, mesomer, racemate, enantiomer, diastereomer or mixture form;
further, the bifeprunox or its derivative includes, but is not limited to, a pharmaceutically acceptable salt, an ether, an ester thereof, a prodrug thereof, a metabolite thereof, a solvate thereof, or a crystal thereof;
further, the bifeprunox or its derivative includes its pharmaceutically acceptable salts including but not limited to hydrochloride, bromate, fumarate, acetate, citrate, sulfate or methanesulfonate;
further, the pharmaceutical composition of bifeprunox or its derivative includes, but is not limited to, tablets, injections, capsules, oral solutions, pills, granules, powders, aerosols, patches, ointments, paints, or suppositories;
further, the pharmaceutical composition of bifeprunox or the derivative thereof also comprises a conventional antitumor drug; further, the conventional antitumor drugs include, but are not limited to, chemotherapeutic drugs, biological targeted therapeutic drugs, metabolic therapeutic drugs, or immunotherapeutic drugs;
further, the effects of the pharmaceutical composition of bifeprunox or its derivatives include, but are not limited to, inhibiting tumor growth and/or metastasis;
further, the pharmaceutical composition of bifeprunox or a derivative thereof is used for treatment including, but not limited to, surgical resection, chemotherapy, or radiation therapy;
further, the bifeprunox, the derivative or the pharmaceutical composition thereof is used for preventing and/or treating breast cancer, esophagus cancer, thyroid cancer, nasopharyngeal cancer, cervical cancer, glioma, prostate cancer, ovarian cancer, lung cancer, colorectal cancer, liver cancer, gastric cancer, melanoma, pancreatic cancer, leukemia and lymphoma;
furthermore, the prevention and/or treatment effect on the breast cancer includes but is not limited to the prevention and/or treatment effect on the breast cancer cell MDA-MB-231 LM 2;
further, the preventive and/or therapeutic effects on esophageal cancer include, but are not limited to, preventive and/or therapeutic effects on esophageal cancer cell EC 109;
further, the preventive and/or therapeutic effect on thyroid cancer includes, but is not limited to, preventive and/or therapeutic effect on thyroid cancer cell TPC-1;
further, the preventive and/or therapeutic effect on nasopharyngeal carcinoma includes, but is not limited to, preventive and/or therapeutic effect on nasopharyngeal carcinoma cells 5-8F;
further, the preventive and/or therapeutic effect on cervical cancer includes, but is not limited to, preventive and/or therapeutic effect on cervical cancer cell SiHa;
further, the prophylactic and/or therapeutic effects on glioma include, but are not limited to, the prophylactic and/or therapeutic effects on glioma cell U251;
further, the preventive and/or therapeutic effect on prostate cancer includes, but is not limited to, preventive and/or therapeutic effect on glioma cell PC-3;
further, prophylactic and/or therapeutic effects on ovarian cancer include, but are not limited to, prophylactic and/or therapeutic effects on ovarian cancer cell a 2780;
further, the preventive and/or therapeutic effect on lung cancer includes, but is not limited to, preventive and/or therapeutic effect on lung cancer cell a 549;
further, the preventive and/or therapeutic effect on intestinal cancer includes, but is not limited to, preventive and/or therapeutic effect on HCT116, which is an intestinal cancer cell;
furthermore, the effect of preventing and/or treating liver cancer includes but is not limited to the effect of preventing and/or treating liver cancer cell SMMC-7721;
further, the preventive and/or therapeutic effect on gastric cancer includes, but is not limited to, preventive and/or therapeutic effect on gastric cancer cell SGC-7901;
further, the prophylactic and/or therapeutic effects on melanoma include, but are not limited to, the prophylactic and/or therapeutic effects on melanoma cell a 375;
further, the preventive and/or therapeutic effects on pancreatic cancer include, but are not limited to, preventive and/or therapeutic effects on pancreatic cancer cells Panc-1;
further, the preventive and/or therapeutic effect on leukemia includes, but is not limited to, preventive and/or therapeutic effect on leukemia cell HL 60;
further, the prophylactic and/or therapeutic effect on lymphoma includes, but is not limited to, the prophylactic and/or therapeutic effect on lymphoma cell MINO.
Drawings
FIG. 1 shows growth inhibition curves of different concentrations of bifeprunox mesylate treated breast cancer cells MDA-MB-231 LM 224 h and 48 h;
FIG. 2 shows growth inhibition curves of different concentrations of bifeprunox mesylate treated esophageal cancer cells EC 10924 h and 48 h;
FIG. 3 shows growth inhibition curves of different concentrations of bifeprunox mesylate-treated thyroid cancer cell lines TPC-124 h and 48 h;
FIG. 4 shows growth inhibition curves of 5- 8F 24h and 48h for nasopharyngeal carcinoma cells treated with bifeprunox mesylate at different concentrations;
FIG. 5 shows growth inhibition curves of SiHa 24h and 48h for cervical cancer cells treated with different concentrations of bifeprunox mesylate;
FIG. 6 shows growth inhibition curves of different concentrations of bifeprunox mesylate treated glioma cells U25124 h and 48 h;
FIG. 7 shows growth inhibition curves of different concentrations of bifeprunox mesylate treated prostate cancer cells PC-324 h and 48 h;
FIG. 8 shows growth inhibition curves of bifeprunox mesylate treated ovarian cancer cells A278024 h and 48h at different concentrations;
FIG. 9 shows growth inhibition curves for different concentrations of bifeprunox mesylate treated lung cancer cells A54924 h and 48 h;
FIG. 10 shows growth inhibition curves of different concentrations of bifeprunox mesylate treated intestinal cancer cells HCT 11624 h and 48 h;
FIG. 11 shows growth inhibition curves of different concentrations of bifeprunox mesylate treated hepatoma cells SMMC-772124 h and 48 h;
FIG. 12 shows growth inhibition curves for different concentrations of bifeprunox mesylate for SGC-790124 h and 48h of gastric adenocarcinoma;
FIG. 13 shows growth inhibition curves for melanoma A37524 h and 48h treated with bifeprunox mesylate at different concentrations;
FIG. 14 shows growth inhibition curves for Panc-124 h and 48h of pancreatic cancer cells treated with different concentrations of bifeprunox mesylate;
FIG. 15 shows growth inhibition curves of different concentrations of bifeprunox mesylate treated leukemia cells HL 6024 h and 48 h;
FIG. 16 shows growth inhibition curves for different concentrations of bifeprunox mesylate treated lymphoma cells MINO for 24h and 48 h.
Advantageous effects
The invention relates to the anti-tumor activity of bifeprunox and derivatives thereof and a new application thereof in preparing a medicament for treating and/or preventing cancers; bifeprunox has obvious and broad-spectrum anti-tumor activity, and has inhibiting effect on tumor cells of multiple human cultured in vitro, such as breast cancer, esophageal cancer, thyroid cancer, nasopharyngeal carcinoma, cervical cancer, glioma, prostatic cancer, ovarian cancer, lung cancer, colorectal cancer, liver cancer, gastric cancer, melanoma, pancreatic cancer, leukemia, lymphoma and other tumors; the bifeprunox and the derivative thereof can be used for preparing antitumor drugs and preventing the occurrence and the metastasis of tumors.
Detailed Description
The invention is described in further detail below with reference to the drawings and the detailed description;
example 1: bifenarimol inhibiting growth of multiple tumor cells
Comparing the cytotoxicity of the bifeprunox mesylate on a human breast cancer cell line MDA-MB-231 LM2, an esophageal cancer cell line EC109, a thyroid cancer cell line TPC-1, a nasopharyngeal cancer cell line 5-8F, a glioma cell line U251, a cervical cancer cell line SiHa, a prostate cancer cell line PC-3, a human colorectal cancer cell line HCT116, a human ovarian cancer cell line A2780, a lung adenocarcinoma cell line A549, a liver cancer cell line SMMC-7721, a stomach adenocarcinoma cell line SGC-7901, a melanoma cell line A375, a pancreatic cancer cell line Panc-1, a leukemia cell line HL60 and a lymphoma cell line MINO by adopting a CCK8 colorimetric method;
the cells were seeded in 96-well plates at 8000 cells/well, and 24h after seeding, the drug was diluted to 0, 0.001, 0.01, 0.1, 1, 10, 20, 40, 80, 160 μ M, and the medium in the original well was discarded, 100 μ L per well was added to the corresponding well, 4 replicate wells per set. After 10 microliter CCK8 is added into each well for incubation for 3 hours during 24 hours and 48 hours respectively, the OD value at A450 is detected by a multifunctional microplate reader, and the inhibition rate is calculated. The results are shown in FIGS. 1-16, and are as follows:
FIG. 1 is the drug sensitivity profiles of the MDA-MB-231 LM 224 h and 48h of the bifeprunox mesylate treated human breast cancer cells, and the IC of 48h5027.23 +/-2.80 mu M; FIG. 2 is a graph of the drug sensitivity of 24h and 48h for esophageal cancer cell EC109 cells treated with bifeprunox mesylate, and the IC of 48h5021.86. + -. 4.37. mu.M. FIG. 3 is a graph showing the drug sensitivity profiles of 24h and 48h for bifeprunox mesylate-treated TPC-1 cells from human thyroid cancer cell lines, and the IC of 48h5037.29 +/-5.01 mu M; FIG. 4 is a graph of Bifenaunox treatment of nasopharyngeal carcinoma 5-8F cells for 24h and 48h drug sensitivity with 48h IC5098.13 +/-30.33 mu M; FIG. 5 is a graph showing the drug sensitivity curve of SiHa cells of cervical cancer cells treated with bifeprunox mesylate for 24h and 48h, and the IC of 48h5036.80 +/-1.67 mu M; FIG. 6 is a graph of the drug sensitivity of bifeprunox mesylate treated glioma cells U251 cells for 24h and 48h with an IC of 48h5030.85 +/-7.6 mu M; FIG. 7 drug sensitivity profiles of Bifenaonol mesylate treated prostate cancer cells PC-324 h and 48h with 48h IC5034.84 +/-3.66 mu M; FIG. 8 drug sensitivity curves of bifeprunox mesylate treated human ovarian cancer A2780 cells for 24h and 48h, and IC of 48h5037.14 +/-1.61 mu M; FIG. 9 drug sensitivity profiles of bifeprunox mesylate-treated lung adenocarcinoma cells A54924 h and 48h, IC of 48h5050.78 +/-2.73 mu M; FIG. 10 is a graph of the drug sensitivity of bifeprunox mesylate on human colorectal cancer cells HCT 11624 h and 48h, and IC of 48h5027.75 +/-2.55 mu M; FIG. 11 is a graph of Bifenarimol-treated hepatoma cells SMMC-772124 h and 48h drug sensitivity with 48h IC5030.1 +/-0.93 mu M; FIG. 12 is bifeprunox mesylate treatmentDrug sensitivity profiles of gastric adenocarcinoma SGC-7901 cells at 24h and 48h, IC at 48h5041.62 +/-3.96 mu M; FIG. 13 is a graph of the drug sensitivity of bifeprunox mesylate on melanoma A375 cells for 24h and 48h with IC for 48h5016.83 +/-4.01 mu M; FIG. 14 is a graph of drug sensitivity of pancreatic cancer cells Panc-1 cells treated with bifeprunox mesylate for 24h and 48h and IC for 48h5045.55 +/-0.70 mu M; FIG. 15 is a graph of the drug sensitivity of the leukemia cells HL60 treated with bifeprunox mesylate at 24h and 48h and the IC at 48h5058.07 +/-1.98 mu M; FIG. 16 is a graph of the drug sensitivity of bifeprunox mesylate on lymphoma cells MINO cells for 24h and 48h with an IC of 48h5021.08. + -. 2.89. mu.M. Therefore, the bifeprunox mesylate has obvious inhibition effects on the growth of breast cancer, esophagus cancer, thyroid cancer, nasopharyngeal carcinoma, cervical cancer, glioma, prostatic cancer, ovarian cancer, lung cancer, colorectal cancer, liver cancer, stomach cancer, melanoma, pancreatic cancer, leukemia and lymphoma cells, and the inhibition effects are dose-dependent and time-dependent;
example 2: in vitro tumor growth inhibition assay
The results are shown in FIGS. 1-16: after 160 mu M of bifeprunox mesylate acts on different tumor cells for 48 hours, the inhibition rates of the tumor cells are 60.68 +/-3.59% (breast cancer cell MDA-MB-231 LM2 shown in figure 1), 75.92 +/-3.09% (esophageal cancer cell EC109 shown in figure 2), 74.20 +/-3.88% (human thyroid cancer cell line TPC-1 shown in figure 3), 41.99 +/-2.56% (nasopharyngeal cancer cell 5-8F shown in figure 4), 74.28 +/-4.02% (cervical cancer cell SiHa shown in figure 5), 69.91 +/-3.85% (glioma cell U251 shown in figure 6), 84.67 +/-0.48% (prostate cancer cell PC-3 shown in figure 7), 69.27 +/-3.50% (human ovarian cancer cell A2780 shown in figure 8), 69.39 +/-1.05% (lung adenocarcinoma cell A shown in figure 9), 73.33 +/-2.67% (human colorectal cancer cell HCT 80 shown in figure 10.84) and SM367721-7721 MC respectively, as shown in fig. 11), 78.20 ± 3.45% (gastric adenocarcinoma SGC-7901 as shown in fig. 12), 73.66 ± 2.57% (melanoma a375 as shown in fig. 13), 65.64 ± 0.68% (pancreatic cancer cell Panc-1 as shown in fig. 14), 81.45 ± 0.40% (leukemia cell HL60 as shown in fig. 15), 87.36 ± 1.48% (lymphoma cell mio as shown in fig. 16). The bifeprunox has good anti-tumor activity in various tumors, and the anti-tumor activity of the bifeprunox can be used for preparing anti-tumor medicaments and medicaments for preventing tumor occurrence and metastasis;
the foregoing detailed description of the preferred embodiments of the invention has been presented. It should be understood that numerous modifications and variations could be devised by those skilled in the art in light of the present teachings without departing from the inventive concepts. Therefore, the technical solutions available to those skilled in the art through logic analysis, reasoning and limited experiments based on the prior art according to the concept of the present invention should be within the scope of protection defined by the claims.
Claims (9)
1. Use of bifeprunox or a derivative thereof, or a pharmaceutical composition comprising bifeprunox or a derivative thereof, in the preparation of a medicament for the prevention and/or treatment of tumors, wherein the bifeprunox is represented by the chemical structural formula (I):
（Ⅰ）
the bifeprunox derivative is shown as a chemical structural formula (II):
（П）
wherein:
R1-R18each independently selected from hydrogen, hydroxy, amino, C1-8Alkyl radical, C1-8Alkoxy radical, C1-8Alcoxyl acyl radical, C2-8Alkenyl radical, C2-8Alkynyl, C1-8Acyl radical, C6-10Aryl radical, C5-6Cycloalkyl, tetrahydropyrroloyl, tetrahydrofuroyl, Ar-C1-4Acyl, Ar-O-C1-4Acyl, Ar-S-C1-4Any one or more of acyl; or R3And R4Or R9And R10Or R14And R15Linked to form a saturated or unsaturated 6-membered carbocyclic or heterocyclic group or an alkyl-substituted carbocyclic or heterocyclic group;
further, C1-8The acyl group is selected from the group consisting of straight or branched alkanoyl, alkenoyl and alkynoyl;
further, Ar is aryl or substituted aryl, and Ar is preferably any one or more of phenyl, benzoyl, naphthyl, pyridyl, furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, pyridazinyl, pyrazinyl, benzofuryl, benzothienyl, indolyl, quinolyl, isoquinolyl, purinyl, benzoxazolyl and benzothiazolyl.
2. The use according to claim 1, wherein said bifeprunox or its derivatives include, but are not limited to, its tautomers, meso-forms, racemates, enantiomers, diastereomers or mixtures thereof.
3. The use according to claim 1 or 2, wherein said bifeprunox or its derivative includes, but is not limited to, its pharmaceutically acceptable salts, ethers, esters, its prodrugs, its metabolites, its solvates or its crystals.
4. Use according to claim 3, wherein said bifeprunox or its derivative including its pharmaceutically acceptable salts includes but is not limited to hydrochloride, bromate, fumarate, acetate, citrate, sulfate or methanesulfonate.
5. Use according to claim 1, wherein the medicament or pharmaceutical composition comprises, but is not limited to, tablets, injections, capsules, oral solutions, pills, granules, powders, aerosols, patches, ointments, paints or suppositories.
6. Use according to claim 1 or 5, wherein the medicament or pharmaceutical composition further comprises a conventional anti-tumor medicament; further, the conventional antitumor drugs include, but are not limited to, chemotherapeutic drugs, biological targeted therapeutic drugs, metabolic therapeutic drugs, or immunotherapeutic drugs.
7. Use according to any one of claims 1 to 3 or 5, wherein the effect of the medicament includes, but is not limited to, inhibition of tumor growth and/or metastasis.
8. The use according to any one of claims 1 to 3 or 5, wherein the medicament or pharmaceutical composition is for use including, but not limited to, surgical resection, chemotherapy or radiation therapy.
9. The use according to any one of claims 1-3, 5, wherein the bifeprunox, its derivative or pharmaceutical composition is used for the prevention and/or treatment of cancer including but not limited to breast cancer, esophageal cancer, thyroid cancer, nasopharyngeal cancer, cervical cancer, glioma, prostate cancer, ovarian cancer, lung cancer, colorectal cancer, liver cancer, stomach cancer, melanoma, pancreatic cancer, leukemia, lymphoma;
still further, the prophylactic and/or therapeutic effects on breast cancer include, but are not limited to, prophylactic and/or therapeutic effects on breast cancer cells MDA-MB-231 LM 2;
still further, the prophylactic and/or therapeutic effect on esophageal cancer includes, but is not limited to, a prophylactic and/or therapeutic effect on esophageal cancer cell EC 109;
still further, the preventive and/or therapeutic effects on thyroid cancer include, but are not limited to, preventive and/or therapeutic effects on thyroid cancer cell TPC-1;
still further, the preventing and/or treating effect on nasopharyngeal carcinoma includes, but is not limited to, preventing and/or treating effect on nasopharyngeal carcinoma cells 5-8F;
still further, the preventive and/or therapeutic effect on cervical cancer includes, but is not limited to, preventive and/or therapeutic effect on cervical cancer cell SiHa;
still further, the prophylactic and/or therapeutic effect on glioma includes, but is not limited to, a prophylactic and/or therapeutic effect on glioma cell U251;
still further, the preventive and/or therapeutic effect on prostate cancer includes, but is not limited to, preventive and/or therapeutic effect on prostate cancer cell PC-3;
still further, the prophylactic and/or therapeutic effect on ovarian cancer includes, but is not limited to, a prophylactic and/or therapeutic effect on ovarian cancer cells A2780;
still further, the preventive and/or therapeutic effect on lung cancer includes, but is not limited to, preventive and/or therapeutic effect on lung cancer cell a 549;
further, the preventive and/or therapeutic effect on intestinal cancer includes, but is not limited to, preventive and/or therapeutic effect on intestinal cancer cell HCT 116;
furthermore, the effect of preventing and/or treating liver cancer includes but is not limited to the effect of preventing and/or treating liver cancer cell SMMC-7721;
further, the preventive and/or therapeutic effect on gastric cancer includes, but is not limited to, preventive and/or therapeutic effect on gastric cancer cell SGC-7901;
still further, the prophylactic and/or therapeutic effect on melanoma includes, but is not limited to, a prophylactic and/or therapeutic effect on melanoma cell a 375;
still further, the prophylactic and/or therapeutic effect on pancreatic cancer includes, but is not limited to, a prophylactic and/or therapeutic effect on pancreatic cancer cells Panc-1;
still further, the prophylactic and/or therapeutic effect on leukemia includes, but is not limited to, a prophylactic and/or therapeutic effect on leukemia cell HL 60;
still further, the prophylactic and/or therapeutic effect on lymphoma includes, but is not limited to, a prophylactic and/or therapeutic effect on lymphoma cell MINO.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997036893A1 (en) * | 1996-03-29 | 1997-10-09 | Duphar International Research B.V. | Piperazine and piperidine compounds |
| CN101918382A (en) * | 2008-01-15 | 2010-12-15 | 雅培卫生保健产品有限责任公司 | Bifeprunox derivatives |
| WO2020210643A1 (en) * | 2019-04-11 | 2020-10-15 | Ian Basil Shine | Cell membrane permeability restoring therapy |
-
2022
- 2022-01-18 CN CN202210052189.3A patent/CN114246869A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997036893A1 (en) * | 1996-03-29 | 1997-10-09 | Duphar International Research B.V. | Piperazine and piperidine compounds |
| CN101918382A (en) * | 2008-01-15 | 2010-12-15 | 雅培卫生保健产品有限责任公司 | Bifeprunox derivatives |
| WO2020210643A1 (en) * | 2019-04-11 | 2020-10-15 | Ian Basil Shine | Cell membrane permeability restoring therapy |
Non-Patent Citations (2)
| Title |
|---|
| BO PAN等: "Modulation by chronic antipsychotic administration of PKA- and GSK3β-mediated pathways and the NMDA receptor in rat ventral midbrain", PSYCHOPHARMACOLOGY, vol. 236, no. 9, pages 2687 - 2697, XP036863339, DOI: 10.1007/s00213-019-05243-x * |
| ROLF W. FEENSTRA等: "New 1-Aryl-4-(biarylmethylene)piperazines as Potential Atypical Antipsychotics Sharing Dopamine D2-Receptor and Serotonin 5-HT1A-Receptor Affinities", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, no. 11, pages 2345 * |
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