CN104193745B - A kind of imidazopyrimidine carboxylic acid compound and preparation method thereof - Google Patents
A kind of imidazopyrimidine carboxylic acid compound and preparation method thereof Download PDFInfo
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- CN104193745B CN104193745B CN201410371409.4A CN201410371409A CN104193745B CN 104193745 B CN104193745 B CN 104193745B CN 201410371409 A CN201410371409 A CN 201410371409A CN 104193745 B CN104193745 B CN 104193745B
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- imidazopyrimidine
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- -1 imidazopyrimidine carboxylic acid compound Chemical class 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229940125782 compound 2 Drugs 0.000 claims abstract description 7
- 229940125904 compound 1 Drugs 0.000 claims abstract description 4
- 229940126214 compound 3 Drugs 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 3
- 150000001408 amides Chemical class 0.000 claims abstract description 3
- 229950010911 orazamide Drugs 0.000 claims abstract description 3
- DVNYTAVYBRSTGK-UHFFFAOYSA-N 5-aminoimidazole-4-carboxamide Chemical compound NC(=O)C=1N=CNC=1N DVNYTAVYBRSTGK-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract description 7
- RAZMBRTXTADRMQ-UHFFFAOYSA-N (4-carbamoyl-1h-imidazol-5-yl)azanium;2,4-dioxo-1h-pyrimidine-6-carboxylate;dihydrate Chemical compound O.O.NC(=O)C=1NC=NC=1N.OC(=O)C1=CC(=O)NC(=O)N1 RAZMBRTXTADRMQ-UHFFFAOYSA-N 0.000 abstract 1
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 abstract 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000012449 Kunming mouse Methods 0.000 description 1
- 101001031591 Mus musculus Heart- and neural crest derivatives-expressed protein 2 Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The present invention relates to a kind of imidazopyrimidine carboxylic acid compound and preparation method thereof, this compound is 8 carboxylic acid imidazos [1,5 a] pyrimidine, preparation method is as follows: (1) compound 1 Orazamide and 1,3 malonaldehyde autoclaves react, under 100 degree, carry out closed loop, form the compound 2 of imidazopyrimidine structure；(2) amide is converted into acid under the conditions of concentrated hydrochloric acid by compound 2, obtains compound 3；Gained end-product has wide application prospect in terms of depression.
Description
Technical field
The present invention relates to compou nd synthesis field, especially a kind of imidazopyrimidine carboxylic acid compound and preparation side thereof
Method.
Background technology
According to 4-Heteroarylimidazo [1,5-a] pyrimidines, U.S. (1983), US 4374988
A19830222 and the application of insecticide；Heterocyclic acyl sulfonamides useful as herbicides
and plant growth regulants,and their compositions and use)U.S.(1989),US
The record of the documents such as 4838925 A19890613, imidazopyrimidine carboxylic acid compound be widely present in have bioactive
In natural product and drug molecule, in terms for the treatment of nervous system disease, there is huge using value, in this compound being
The derivant of mesosome synthesis, much having proved to be can be for synthesizing the bioactive compound for the treatment of nervous system disease.
Visible, the pharmacologically active good due to it and potential medical value, the synthesis of present stage imidazopyrimidine carboxylic acid compound
Receive much attention.
Summary of the invention
The technical problem to be solved is to provide a kind of imidazopyrimidine carboxylic acid compound.
Another technical problem to be solved by this invention is to provide the preparation of above-mentioned imidazopyrimidine carboxylic acid compound
Method.
For solving above-mentioned technical problem, the technical scheme is that
A kind of imidazopyrimidine carboxylic acid compound, 8-carboxylic acid-imidazolide also [1,5-a] pyrimidine, its structural formula is (I) institute
Show,
Preferably, above-mentioned imidazopyrimidine carboxylic acid compound, 8-carboxylic acid-imidazolide also [1,5-a] pyrimidine is that bronzing is solid
Body, its hydrogen nuclear magnetic resonance modal data is 1H-NMR (DMSO；400MHZ)7.656(b,1H)8.44(d,1H)8.68(b,1H)9.55
(b,1H)。
The preparation method of above-mentioned imidazopyrimidine carboxylic acid compound, specifically comprises the following steps that
(1) compound 1 Orazamide and 1,3-malonaldehyde autoclave reacts, and carries out closed loop under 100 degree, forms imidazoles
And the compound 2 of pyrimidine structure；
(2) amide is converted into acid under the conditions of concentrated hydrochloric acid by compound 2, obtains compound 3, wherein,
Preferably, the preparation method of above-mentioned imidazopyrimidine carboxylic acid compound, described compound 2 as intermediate product,
For noval chemical compound.
The concrete reaction equation of the preparation method of above-mentioned imidazopyrimidine carboxylic acid compound is as follows:
The invention has the beneficial effects as follows:
The preparation method of above-mentioned imidazopyrimidine carboxylic acid compound, is a kind of cheaper starting materials, simple 8-of synthetic method
The preparation method of carboxylic acid-imidazolide's also [1,5-a] pyrimidine, its product 8-carboxylic acid-imidazolide also [1,5-a] pyrimidine is in terms of depression
There is wide application prospect.
Accompanying drawing explanation
Fig. 1 is the HNMR spectrogram of 8-carboxylic acid-imidazolide also [1,5-a] pyrimidine.
Detailed description of the invention
In order to make those skilled in the art be better understood from technical scheme, below in conjunction with detailed description of the invention
Technical scheme of the present invention is described in further detail.
Embodiment 1
A kind of preparation method of imidazopyrimidine carboxylic acid compound 8-carboxylic acid-imidazolide also [1,5-a] pyrimidine, concrete steps
As follows:
(1) by 35g compound 1 and 49g1,3-malonaldehyde (compound 1a) joins in 400mL ethanol, and autoclave reacts
100 spend night (20 hours)；Being cooled to room temperature, filter, with 200mL ethanol filter wash cake once, filter cake oil pump draws dry chemical combination
Thing 2 (sterling) 40 grams, productivity 100%, black solid.TLC information: raw material Rf=0.6, compound 2Rf=0.4, developing solvent: four
Hydrogen furan: water=20:1.
(2) joining in 350mL concentrated hydrochloric acid by 24g compound 2,100 degree flow through night (20 hours) next time；Draw dry solvent,
Crossing pillar (200-300 mesh silicon gel column) purification and obtain compound 31.3 grams, productivity 5.4%, for red brown solid.TLC information: former
Material Rf=0.4, product Rf=0.7, developing solvent: oxolane: water=20:1.After measured, as it is shown in figure 1, its hydrogen modal data is
1H-NMR(DMSO；400MHZ)7.656(b,1H)8.44(d,1H)8.68(b,1H)9.55(b,1H).
Preparation process described in embodiment 1 is as follows:
Application test example
Kun Ming mice, body weight 20-22g, white mice is raised in the quiet environment that cleaning ventilation, light and shade circulate,
Ad lib is drunk water.Experiment is divided into two groups, often group 10, and every treated animal oral administration, wherein, matched group is Quetiapine 10mg/
Kg, test group are embodiment 1 gained final product compound 35mg/kg.After administration, every animal is placed in glass jar gently
(storing full water in cylinder), mice is swum 6 minutes, the dead time (second) accumulative in recording latter 4 minutes.Data acquisition SPSS12.0 unites
Meter software processes.Result of the test shows, the control group mice dead time is 159 ± 11 seconds, and the test group mice dead time is 98
± 11 seconds.Result illustrates, embodiment 1 gained compound 3 has antidepressant effect.
Above-mentioned with reference to detailed description of the invention, this kind of imidazopyrimidine carboxylic acid compound and preparation method thereof is carried out
Describe in detail, be illustrative rather than determinate, can according to restriction scope list several embodiments, therefore not
Depart from changing and modifications, within protection scope of the present invention should being belonged under present general inventive concept.
Claims (1)
1. the preparation method of an imidazopyrimidine carboxylic acid compound, it is characterised in that: specifically comprise the following steps that
(1) compound 1 Orazamide and 1,3-malonaldehyde autoclave reacts, and carries out closed loop under 100 degree, forms imidazo phonetic
The compound 2 of pyridine structure；
(2) amide is converted into acid under the conditions of concentrated hydrochloric acid by compound 2, obtains compound 3, wherein,
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| CN104193745B true CN104193745B (en) | 2016-09-28 |
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| CN105061433A (en) * | 2015-07-24 | 2015-11-18 | 河南紫罗兰科技有限公司 | Synthetic method for 5-bromo-imidazo[1, 2-A]pyrimidine-3-carboxylate and corresponding acid thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4963552A (en) * | 1989-08-28 | 1990-10-16 | American Cyanamid Company | 1-substitute-1,2-dihydro-4-((substituted)phenyl)imidazo-[1,5-a]pyrimidine-8-carbonitriles |
| CN1409713A (en) * | 1999-12-13 | 2003-04-09 | 卫材株式会社 | Fused heterotricyclic compound, process for preparing compounds and drugs containing the same |
| CN1649848A (en) * | 2001-04-30 | 2005-08-03 | 葛兰素集团有限公司 | Fused pyrimidines derivatives as antagonists of the corticotropin releasing factor (CRF) |
| CN1826345A (en) * | 2003-07-25 | 2006-08-30 | 神经能质公司 | Imidazo-pyrimidines and triazolo-pyrimidines: benzodiazepine receptor ligands |
| CN1890242A (en) * | 2003-10-03 | 2007-01-03 | 弗·哈夫曼-拉罗切有限公司 | Pyrazolo and imidazo-pyrimidine derivatives |
| WO2011036889A1 (en) * | 2009-09-25 | 2011-03-31 | 武田薬品工業株式会社 | Heterocyclic compound |
-
2014
- 2014-07-30 CN CN201410371409.4A patent/CN104193745B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4963552A (en) * | 1989-08-28 | 1990-10-16 | American Cyanamid Company | 1-substitute-1,2-dihydro-4-((substituted)phenyl)imidazo-[1,5-a]pyrimidine-8-carbonitriles |
| CN1409713A (en) * | 1999-12-13 | 2003-04-09 | 卫材株式会社 | Fused heterotricyclic compound, process for preparing compounds and drugs containing the same |
| CN1649848A (en) * | 2001-04-30 | 2005-08-03 | 葛兰素集团有限公司 | Fused pyrimidines derivatives as antagonists of the corticotropin releasing factor (CRF) |
| CN1826345A (en) * | 2003-07-25 | 2006-08-30 | 神经能质公司 | Imidazo-pyrimidines and triazolo-pyrimidines: benzodiazepine receptor ligands |
| CN1890242A (en) * | 2003-10-03 | 2007-01-03 | 弗·哈夫曼-拉罗切有限公司 | Pyrazolo and imidazo-pyrimidine derivatives |
| WO2011036889A1 (en) * | 2009-09-25 | 2011-03-31 | 武田薬品工業株式会社 | Heterocyclic compound |
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