CN109549941A - A kind of purposes of Pyrazolopyrimidine derivative in terms of disease medicament is treated in preparation - Google Patents
A kind of purposes of Pyrazolopyrimidine derivative in terms of disease medicament is treated in preparation Download PDFInfo
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- CN109549941A CN109549941A CN201710878592.0A CN201710878592A CN109549941A CN 109549941 A CN109549941 A CN 109549941A CN 201710878592 A CN201710878592 A CN 201710878592A CN 109549941 A CN109549941 A CN 109549941A
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- cancer
- glioma
- pyrazolopyrimidine derivative
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- carcinoma
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- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical class C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 title claims abstract description 22
- 201000010099 disease Diseases 0.000 title claims abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 14
- 239000003814 drug Substances 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
- 206010018338 Glioma Diseases 0.000 claims abstract description 19
- 208000032612 Glial tumor Diseases 0.000 claims abstract description 17
- 201000011510 cancer Diseases 0.000 claims abstract description 11
- 208000037845 Cutaneous squamous cell carcinoma Diseases 0.000 claims abstract description 5
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims abstract description 5
- 210000004252 chorionic villi Anatomy 0.000 claims abstract description 5
- 201000010106 skin squamous cell carcinoma Diseases 0.000 claims abstract description 5
- 206010005003 Bladder cancer Diseases 0.000 claims abstract description 3
- 201000009030 Carcinoma Diseases 0.000 claims abstract description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims abstract description 3
- 208000002454 Nasopharyngeal Carcinoma Diseases 0.000 claims abstract description 3
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims abstract description 3
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 3
- 208000006265 Renal cell carcinoma Diseases 0.000 claims abstract description 3
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims abstract description 3
- 208000006990 cholangiocarcinoma Diseases 0.000 claims abstract description 3
- 210000003734 kidney Anatomy 0.000 claims abstract description 3
- 210000004072 lung Anatomy 0.000 claims abstract description 3
- 201000005202 lung cancer Diseases 0.000 claims abstract description 3
- 208000020816 lung neoplasm Diseases 0.000 claims abstract description 3
- 201000011216 nasopharynx carcinoma Diseases 0.000 claims abstract description 3
- 208000015347 renal cell adenocarcinoma Diseases 0.000 claims abstract description 3
- 210000001550 testis Anatomy 0.000 claims abstract description 3
- 201000005112 urinary bladder cancer Diseases 0.000 claims abstract description 3
- 208000006332 Choriocarcinoma Diseases 0.000 claims abstract 3
- 206010003571 Astrocytoma Diseases 0.000 claims description 2
- 206010014967 Ependymoma Diseases 0.000 claims description 2
- 208000000172 Medulloblastoma Diseases 0.000 claims description 2
- 201000010133 Oligodendroglioma Diseases 0.000 claims description 2
- 208000007641 Pinealoma Diseases 0.000 claims description 2
- 201000004058 mixed glioma Diseases 0.000 claims description 2
- 230000001537 neural effect Effects 0.000 claims description 2
- 208000003154 papilloma Diseases 0.000 claims description 2
- 208000024724 pineal body neoplasm Diseases 0.000 claims description 2
- 201000004123 pineal gland cancer Diseases 0.000 claims description 2
- 210000002165 glioblast Anatomy 0.000 claims 1
- 210000004027 cell Anatomy 0.000 abstract description 15
- 230000002401 inhibitory effect Effects 0.000 abstract description 12
- 210000004881 tumor cell Anatomy 0.000 abstract description 8
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 abstract description 7
- 239000005511 L01XE05 - Sorafenib Substances 0.000 abstract description 7
- 229960003787 sorafenib Drugs 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 5
- 210000004443 dendritic cell Anatomy 0.000 abstract description 2
- 238000002474 experimental method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 210000000988 bone and bone Anatomy 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 101000932478 Homo sapiens Receptor-type tyrosine-protein kinase FLT3 Proteins 0.000 description 2
- 102100020718 Receptor-type tyrosine-protein kinase FLT3 Human genes 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 210000000806 cranial fontanelle Anatomy 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 210000004761 scalp Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
- 241000973495 Odax pullus Species 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000256856 Vespidae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000001467 acupuncture Methods 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001348 anti-glioma Effects 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 201000007983 brain glioma Diseases 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
Abstract
The present invention relates to technical field of pharmaceuticals, purposes of especially a kind of Pyrazolopyrimidine derivative in terms of disease medicament is treated in preparation.The disease includes myelodysplastic syndrome, oophoroma, carcinoma of testis, cutaneous squamous cell carcinoma, bladder cancer, cholangiocarcinoma, prostate cancer, glioma, nasopharyngeal carcinoma, kidney, Dendritic cell, lung squamous cancer, maxicell lung cancer, renal cell adenocarcinoma, choriocarcinoma, placental villi cancer.Pyrazolopyrimidine derivative of the present invention has apparent inhibiting effect to kinds of tumor cells, especially more obvious to the inhibiting tumour cells effect of glioma, is better than Sorafenib to the inhibitory effect of Partial tumors cell.
Description
Technical field
The present invention relates to technical field of pharmaceuticals, especially a kind of Pyrazolopyrimidine derivative treats disease medicament side in preparation
The purposes in face.
Background technique
Sorafenib (sorafenib) is clinically using more extensive FLT3 inhibitor, but not about rope
La Feini is applied to the report of the purposes of brain glioma.
Pyrazolopyrimidine derivative (formula I) is a kind of targeting in the micromolecular inhibitor of FLT3 kinases, is applicant
The new compound of independent research, compound patent has been obtained for authorizing at present.
The current only report about Pyrazolopyrimidine derivative in terms for the treatment of acute myeloid leukaemia and psoriasis.
Summary of the invention
In order to overcome the shortcomings of the prior art, the present invention provides Pyrazolopyrimidine derivative and treats disease medicine in preparation
The purposes in object space face.
The purpose of the present invention can be achieved through the following technical solutions:
A kind of purposes of the Pyrazolopyrimidine derivative as shown in formula I in terms of disease medicament is treated in preparation
The disease include the following: myelodysplastic syndrome, oophoroma, carcinoma of testis, cutaneous squamous cell carcinoma, bladder
Cancer, cholangiocarcinoma, prostate cancer, glioma, nasopharyngeal carcinoma, kidney, Dendritic cell, lung squamous cancer, maxicell lung cancer, renal cell adenocarcinoma, suede
Trichilemma cancer, placental villi cancer.
Preferably, the disease include the following: myelodysplastic syndrome, cutaneous squamous cell carcinoma, glioma, villus
Film cancer, placental villi cancer.
Preferably, the disease is glioma.
The glioma include astrocytoma, glioblastoma, medulloblastoma, ependymoma, oligodendroglioma,
Pinealoma, Mixed Gliomas, papilloma choroideum, unfiled glioma and neuronal tumour.
Compared with the prior art, the method have the advantages that:
1. Pyrazolopyrimidine derivative of the present invention has apparent inhibiting effect to kinds of tumor cells, especially to glioma
Inhibiting tumour cells effect it is more obvious, Sorafenib is better than to the inhibitory effect of Partial tumors cell.
2. Pyrazolopyrimidine derivative of the present invention is substantially better than Sorafenib to the inhibiting effect effect of glioma growth.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..
The external human tumor cells proliferation inhibition test of the Pyrazolopyrimidine derivative of the present invention of embodiment 1
(1) experimental material: cell strain used in this experiment is purchased from ATCC company, the U.S. or Chinese Academy of Sciences typical case culture
Object preservation committee cell bank, condition of culture condition to specifications.Pyrazolopyrimidine derivative is synthesized by inventor.
(2) experimental method: collecting the cell to be measured for being in logarithmic growth phase, (depending on visual cell, is hanged with every hole fixed number
Floating cell is generally 1 × 104-4×104Cell number/hole, attached cell are generally 2 × 103-4×103Cell number/hole) it is inoculated in
In 96 orifice plates, the overnight incubation in 37 DEG C, the cell incubator of 5%CO2.Next day, diluted respectively with culture medium Sorafenib and
Pyrazolopyrimidine derivative is to respective concentration and is added in 96 orifice plate corresponding apertures, 3 multiple holes of each sample, while solvent is arranged
Control group and blank control group containing only culture medium, 96 orifice plates after dosing are continued to be put into cell incubator and cultivate 72h.
After 72h, 20 μ LMTT solution (5mg/mL) are added into the every hole of 96 orifice plates, and be incubated for 2-4h in cell incubator, are then added
The acid sodium dodecyl sulfate solution of 50 μ L 20%, Rong Xie formazan is stayed overnight at 37 DEG C, with microplate reader under 570nm wavelength
Absorbance is detected, and calculates drug according to the following formula to the growth inhibition ratio of cell.
Inhibiting rate=[(C-X)/(C-C0)] × 100%
Wherein, C, C0The mean absorbance values of solvent control group, blank control group and drug-treated group are respectively represented with X.
Finally, being fitted growth inhibition curve using 5.0 software of Graphpad Prism and calculating IC50Value.IC5010 μM of <, which is then represented, to be had
Inhibitory activity.
(3) experimental result
Influence of 1 Pyrazolopyrimidine derivative of table to various tumour cells
Embodiment 2 intends anti-glioma experiment in vivo
(1) experimental material: C 6 glioma cell of rat strain (Shanghai Inst. of Life Science, CAS cellular resources
Center)；Healthy male SD rat, SPF grades.Pyrazolopyrimidine derivative is synthesized by inventor.
(2) experimental method:
The foundation of rat glioma model: it after SD rat tail vein injects 1% yellow Jackets (40mg/kg), sloughs big
Mouse overhead hair laterally cuts scalp, exposure anterior fontanelle skull mark, anterior fontanelle after the bilateral palpebral fissure line of the crown at about 1.5cm
1mm before midpoint is opened by sagittal suture and is bored a bone hole with self-control dental drill at 3mm, and micro syringe extracts 10 μ L of C6 cell suspension, vertically
It is fixed on testing stand, through 6mm under inserting needle endocranium at green bone hole, retreats 1mm, in cell suspension has been infused (2 μ L/ in 10min
Min), let the acupuncture needle remain at a certain point after injection 5min, the slow withdraw of the needle, bone wax close bone hole, No. 1 silk suture incision of scalp.
Rat is randomly divided into model group, Pyrazolopyrimidine derivative low dose group (1mg/kg/d), pyrazolopyrimidine to spread out
Biological middle dose group (3mg/kg/d), Pyrazolopyrimidine derivative high dose group (10mg/kg/d), comparison medicine group (Sorafenib,
3mg/kg/d), every group 15.Medicine group starts the oral drug for giving matched doses after rat postoperative 2 days, and model group is then given
Give the physiological saline of equivalent, continuous 21 days.
It after administration, is anaesthetized with overdose of sodium pentobarbital and puts to death experimental animal, broken end takes brain, and full brain is in 3% formaldehyde
1 week is fixed, makees coronal incision along entry point, measures the line of apsides of tumour, calculates gross tumor volume V=π ab2/ 6 (b is minor axis).Suppression
Average external volume × 100% of ratio of outflow/%=(gross tumor volume-experimental group gross tumor volume of model group)/model group tumour inhibits
Rate > 30% is tumour to medicaments insensitive.
Numerical value indicates that test data is for statistical analysis with SPSS 17.0 with average ± standard deviation, and group difference is used
ANOVA is examined.
(3) experimental result
Influence of the table 2 to rat tumor volume and tumour inhibiting rate
Conclusion
In vitro cell experiment shows that Pyrazolopyrimidine derivative of the present invention has apparent inhibition to make to kinds of tumor cells
With, it is especially more obvious to the inhibiting tumour cells effect of glioma, Suo Lafei is better than to the inhibitory effect of Partial tumors cell
Buddhist nun.Zoopery shows that Pyrazolopyrimidine derivative can effectively inhibit the colloid knurl of rat to grow, and effect is better than Suo Lafei
Buddhist nun.
Although above having used general explanation, specific embodiment and test, the present invention is made to retouch in detail
It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Range.
Claims (5)
1. a kind of purposes of Pyrazolopyrimidine derivative as shown in formula I in terms of disease medicament is treated in preparation
2. purposes according to claim 1, which is characterized in that the disease include the following: myelodysplastic syndrome,
Oophoroma, carcinoma of testis, cutaneous squamous cell carcinoma, bladder cancer, cholangiocarcinoma, prostate cancer, glioma, nasopharyngeal carcinoma, kidney, tongue squama
Cancer, lung squamous cancer, maxicell lung cancer, renal cell adenocarcinoma, choriocarcinoma, placental villi cancer.
3. purposes according to claim 2, which is characterized in that the disease include the following: myelodysplastic syndrome,
Cutaneous squamous cell carcinoma, glioma, choriocarcinoma, placental villi cancer.
4. purposes according to claim 3, which is characterized in that the disease is glioma.
5. purposes according to claim 4, which is characterized in that the glioma includes astrocytoma, glioblast
It is tumor, medulloblastoma, ependymoma, oligodendroglioma, pinealoma, Mixed Gliomas, papilloma choroideum, unfiled
Glioma and neuronal tumour.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710878592.0A CN109549941A (en) | 2017-09-26 | 2017-09-26 | A kind of purposes of Pyrazolopyrimidine derivative in terms of disease medicament is treated in preparation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710878592.0A CN109549941A (en) | 2017-09-26 | 2017-09-26 | A kind of purposes of Pyrazolopyrimidine derivative in terms of disease medicament is treated in preparation |
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| Publication Number | Publication Date |
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| CN109549941A true CN109549941A (en) | 2019-04-02 |
Family
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| CN201710878592.0A Pending CN109549941A (en) | 2017-09-26 | 2017-09-26 | A kind of purposes of Pyrazolopyrimidine derivative in terms of disease medicament is treated in preparation |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110894494A (en) * | 2019-11-22 | 2020-03-20 | 广西梧州制药（集团）股份有限公司 | Method for large-scale high-density suspension culture of 293 cell high-yield adenovirus |
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|---|---|---|---|---|
| CN101208310A (en) * | 2005-07-20 | 2008-06-25 | 千禧药品公司 | New crystal forms of 4-[6-methoxy-7-(3-piperidin-1-yl-propoxy)quinazolin-4-yl]piperazine-1-carboxylic acid(4-isopropoxyphenyl)-amide |
| CN104703623A (en) * | 2012-03-19 | 2015-06-10 | 普莱希科公司 | Compounds and methods for kinase modulation, and indications therefor |
-
2017
- 2017-09-26 CN CN201710878592.0A patent/CN109549941A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101208310A (en) * | 2005-07-20 | 2008-06-25 | 千禧药品公司 | New crystal forms of 4-[6-methoxy-7-(3-piperidin-1-yl-propoxy)quinazolin-4-yl]piperazine-1-carboxylic acid(4-isopropoxyphenyl)-amide |
| CN104703623A (en) * | 2012-03-19 | 2015-06-10 | 普莱希科公司 | Compounds and methods for kinase modulation, and indications therefor |
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| Title |
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| GUO-BO LI 等: "Drug Discovery against Psoriasis: Identification of a New Potent FMSlikeTyrosineKinase3(FLT3)Inhibitor,1 (4-((1H Pyrazolo[3,4 d]pyrimidin-4-yl)oxy)-3-fluorophenyl)-3- (5 (tertbutyl)isoxazol-3-yl)urea, That Showed Potent Activity in a Psoriatic Animal Model" * |
| 吴泽斌;郭东生;雷霆;: "血小板源生长因子及其在胶质瘤靶向治疗中的研究现状" * |
| 姚磊，等: "FLT3抑制剂的抗肿瘤研发现状" * |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110894494A (en) * | 2019-11-22 | 2020-03-20 | 广西梧州制药（集团）股份有限公司 | Method for large-scale high-density suspension culture of 293 cell high-yield adenovirus |
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Application publication date: 20190402 |