CN105820053A - Pharmaceutical composition of cefalexin and application of pharmaceutical composition in biological medicine - Google Patents
Pharmaceutical composition of cefalexin and application of pharmaceutical composition in biological medicine Download PDFInfo
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- CN105820053A CN105820053A CN201610258255.7A CN201610258255A CN105820053A CN 105820053 A CN105820053 A CN 105820053A CN 201610258255 A CN201610258255 A CN 201610258255A CN 105820053 A CN105820053 A CN 105820053A
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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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
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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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
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Abstract
The invention discloses a pharmaceutical composition of cefalexin and pharmaceutical of the pharmaceutical composition in a biological medicine. The pharmaceutical composition of cefalexin, which is disclosed by the invention, comprises cefalexin and a natural product compound (I) having a novel structure, cefalexin and the compound (I) both have remarkable anti-depression functions, and moreover, with the combination of cefalexin and the compound, the anti-depression effect can be remarkably improved, an anti-depression medicine can be developed, and compared with the prior art, the pharmaceutical composition has outstanding practical characteristics and remarkable improvement.
Description
Technical field
The invention belongs to biomedicine field, relate to the new application of cefalexin, be specifically related to the pharmaceutical composition of cefalexin and the application in biological medicine thereof.
Background technology
Cefalexin can suppress the synthesis of cell wall, makes cellular content be expanded to rupture dissolving, kills antibacterial.
Up to now, there is not yet the dependency report of cefalexin and pharmaceutical composition thereof and depression.
Summary of the invention
It is an object of the invention to provide the pharmaceutical composition of a kind of cefalexin, containing cefalexin and the natural product of a kind of novel structure in this pharmaceutical composition, cefalexin and this natural product can be with Synergistic treatment depressions.
The above-mentioned purpose of the present invention is achieved by techniques below scheme:
A kind of compound (I) with following structural formula,
The pharmaceutical composition of a kind of cefalexin, including cefalexin, compound as claimed in claim 1 (I) and pharmaceutically acceptable carrier, is prepared as the dosage form needed.
Further, pharmaceutically acceptable carrier includes diluent, excipient, filler, binding agent, wetting agent, disintegrating agent, absorption enhancer, surfactant, absorption carrier or lubricant.
Further, described dosage form includes tablet, capsule, oral liquid, sucks agent, granule, electuary, pill, powder, unguentum, sublimed preparation, suspensoid, powder, solution, injection, suppository, spray, drop or patch.
The preparation method of above-claimed cpd (I), comprise following operating procedure: Herba Andrographis is pulverized by (a), with 65～85% alcohol heat reflux extract, united extraction liquid, it is concentrated into without alcohol taste, successively with petroleum ether, ethyl acetate and water saturated n-butanol extraction, respectively obtain petroleum ether extract, acetic acid ethyl ester extract and n-butyl alcohol extract；B n-butyl alcohol extract macroporous resin remove impurity in () step (a), first with 8 column volumes of 6% ethanol elution, then with 8 column volumes of 70% ethanol elution, collects 70% eluent, concentrating under reduced pressure obtains 70% ethanol elution concentrate；C in () step (b), 70% ethanol elution concentrate purification on normal-phase silica gel separates, obtain 4 components with the methylene chloride-methanol gradient elution that volume ratio is 50:1,25:1,15:1 and 5:1 successively；D in () step (c), component 4 separates further by purification on normal-phase silica gel, obtain 3 components with the methylene chloride-methanol gradient elution that volume ratio is 10:1,5:1 and 2:1 successively；E reverse phase silica gel that in () step (d), component 2 is bonded by octadecylsilane separates, with the methanol aqueous solution isocratic elution that concentration expressed in percentage by volume is 75%, collecting 8～14 column volume eluents, eluent is concentrated under reduced pressure to give compound (I).
Further, in the preparation method of compound (I), step (a) is extracted with 75% alcohol heat reflux, united extraction liquid.
Further, in the preparation method of compound (I), described macroporous resin is AB-8 type macroporous adsorbent resin.
Further, in the preparation method of compound (I), step (a) replaces ethyl acetate to extract with dichloromethane, obtains dichloromethane extract.
The above-claimed cpd (I) application in the medicine of preparation treatment depression.
The application in the medicine of preparation treatment depression of the pharmaceutical composition of above-mentioned cefalexin.
Advantages of the present invention: containing cefalexin and the natural product of a kind of novel structure in the pharmaceutical composition of the cefalexin that the present invention provides, when cefalexin and this natural product independent role, has therapeutical effect to depression；During the two synergy, the therapeutic effect of depression is improved further, the medicine for the treatment of depression can be developed into.
Detailed description of the invention
Embodiment 1: compound (I) separates preparation and structural identification
Separation method: Herba Andrographis (3kg) is pulverized by (a), (20L × 3 time) are extracted with 75% alcohol heat reflux, united extraction liquid, it is concentrated into without alcohol taste (4L), successively with petroleum ether (4L × 3 time), ethyl acetate (4L × 3 time) and water saturated n-butyl alcohol (4L × 3 time) extraction, respectively obtain petroleum ether extract, acetic acid ethyl ester extract and n-butyl alcohol extract；B n-butyl alcohol extract AB-8 type macroporous resin remove impurity in () step (a), first with 8 column volumes of 6% ethanol elution, then with 8 column volumes of 70% ethanol elution, collects 70% eluent, concentrating under reduced pressure obtains 70% ethanol elution concentrate；C in () step (b), 70% ethanol elution concentrate purification on normal-phase silica gel separates, successively with volume ratio be 50:1 (8 column volumes), the methylene chloride-methanol gradient elution of 25:1 (8 column volumes), 15:1 (8 column volumes) and 5:1 (10 column volumes) obtain 4 components；D in () step (c), component 4 separates further by purification on normal-phase silica gel, successively with volume ratio be 10:1 (8 column volumes), the methylene chloride-methanol gradient elution of 5:1 (10 column volumes) and 2:1 (5 column volumes) obtain 3 components；E reverse phase silica gel that in () step (d), component 2 is bonded by octadecylsilane separates, with the methanol aqueous solution isocratic elution that concentration expressed in percentage by volume is 75%, collecting 8～14 column volume eluents, eluent concentrating under reduced pressure obtains compound (I) (HPLC normalization purity is more than 98%).
Structural identification: HR-ESI-MS shows [M+Na]+For m/z473.2153, can obtain molecular formula in conjunction with nuclear-magnetism feature is C24H34O8, degree of unsaturation is 8.Hydrogen nuclear magnetic resonance modal data δH(ppm, CDCl3null，500MHz): H-1a (1.27，m)，H-1b(1.51，m)，H-2a(1.81，m)，H-2b(1.93，m)，H-3(5.91，br，s)，H-5(3.02，d，J=1.3Hz)，H-6(6.83，d，J=1.3Hz)，H-9(2.36，m，2H)，H-12(1.44，s)，H-13(1.47，s)，H-14(0.99，s)，H-15(1.56，s)，H-3’(5.14，q，J=6.3Hz)，H-4’(1.32，d，J=6.3Hz)，H-5a’(6.33，d，J=12.3Hz)，H-5b’(6.62，d，J=12.3Hz)，4-AcO(1.96，s)，3’-AcO(1.99，s)；Carbon-13 nmr spectra data δC(ppm, CDCl3, 125MHz): 31.8 (CH2, 1-C), 22.8 (CH2, 2-C), 73.6 (CH, 3-C), 83.0 (C, 4-C), 47.9 (CH, 5-C), 145.7 (CH, 6-C), 140.6 (C, 7-C), 201.1 (C, 8-C), 57.8 (CH2, 9-C), 39.4 (C, 10-C), 71.4 (C, 11-C), 29.3 (CH3, 12-C), 28.5 (CH3, 13-C), 18.3 (CH3, 14-C), 18.9 (CH3, 15-C), 167.8 (C, 1 '-C), 138.6 (C, 2 '-C), 65.1 (CH, 3 '-C), 19.3 (CH3, 4 '-C), 127.2 (CH2, 5 '-C), 169.9 (C, 4-AcO), 21.5 (CH3, 4-AcO), 170.4 (C, 3 '-AcO), 22.4 (CH3, 3 '-AcO).1757cm in infrared spectrum-1With 1648cm-1Absorption band shows to there is carbonyl and double bond fragment in structure.13C-NMR, DEPT and hsqc spectrum show 24 carbon signals, including seven methyl, four methylene (an alkene carbon), four methines (two company's oxygen carbon and an alkene carbon), and nine quaternary carbons (four carbonyl carbon, two alkene carbon and two oxygen-containing quaternary carbons).In conjunction with insatiable hunger sum, function above structure shows that this compound is twin nuclei.1H-NMR spectrum combines hsqc spectrum and shows five methyl proton signal δH0.99 (3H, s), 1.32 (3H, d, J=6.3Hz), 1.44 (3H, s), 1.47 (3H, s), 1.56 (3H, s), two acetylmethyl proton signal δH1.96 (3H, s) with 1.99 (3H, s), an olefinic methene proton signal δH6.33 (1H, d, J=12.3Hz) and 6.62 (1H, d, J=12.3Hz), two company oxygen methine proton signal δH5.91 (1H, s) with 5.14 (1H, q, J=6.3H), an olefinic methine proton signal δH6.83 (1H, d, J=1.3Hz), above NMR data can confirm that this compound is fetid marsh fleabane ketone derivatives.H in HMBC spectrum3-12 with C-11, H3-13 with C-11, H3-14 with C-10, H3The coherent signal of-15 and C-4 can be attributed to the fragment on fetid marsh fleabane ketone, and it is esterified that C-3 position proton signal shifts to low field explanation C-3 hydroxyl, and H-3 with the C-1 ' coherent signal in being composed by HMBC is further confirmed that.H-3 ' and 3 '-AcO, C-2 ' and C-4 ' and H in being composed by HMBC2-5 ' and C-2 ' and C-1 ' coherent signal can confirm that existence 3 '-acetyl group-2 in structure '-alkene-butyryl acyloxy side chain structure.C-11(δC71.4) chemical shift of position shows that it is connected with a hydroxyl.H in NOESY spectrumβ-1/H3-14, Hβ-1/H-3, H-3/H3-15 and H3-14/H3The coherent signal of-15 shows H-3, H3-14 and H3-15 at the homonymy of fetid marsh fleabane ketone skeleton, H in additionα-1/H-5 coherent signal hint H-5 is at H-3 and H3The heteropleural of-14.The relative configuration of this compound is confirmed by X-single crystal diffraction further, and the absolute configuration of C-3 position be can confirm that as R configuration by acidolysis reaction and Mosher method.Comprehensive hydrogen spectrum, carbon spectrum, HMBC spectrum and NOESY spectrum, and document is about correlation type nuclear magnetic data, can substantially determine that this compound is as follows, spatial configuration is determined by ECD test further, and theoretical value is basically identical with experiment value.This compound chemical formula and carbon atoms numbered are as follows:
Embodiment 2: pharmacological action
1, materials and methods
1.1 animal
Laboratory animal SPF level kunming mice, male and female half and half, body weight 18～22g, purchased from Traditional Chinese Medicine University Of Guangzhou's Experimental Animal Center.
1.2 medicines and reagent
Cefalexin is purchased from Nat'l Pharmaceutical & Biological Products Control Institute, and compound (I) is made by oneself, and preparation method is shown in embodiment 1.Fluoxetine hydrochloride capsules (fluoxetine) (Li Lai Suzhou pharmaceutical Co. Ltd product, specification: 20mg/ sheet)；Noradrenaline bitartrate (NE)；Epinephrine (E)；Dopamine hydrochloride (DA)；5-hydroxy tryptamine hydrochlorate (5-HT)；Above 5 kinds of reference substances are purchased from Nat'l Pharmaceutical & Biological Products Control Institute's (for assay)；Acetonitrile (chromatographically pure, Australia Science and Technology Ltd. of immigration office)；Perfluorooctane sulfonate (B8, analytical pure, Tianjin great Mao chemical reagent factory)；Perchloric acid (analytical pure, Guangzhou Chemical Reagent Factory)；Sodium dihydrogen phosphate (analytical pure, Guangzhou Chemical Reagent Factory).
1.3 key instrument
Tail suspension experiment device is made by oneself, wooden stick is isolated into 2 districts with cardboard, uses immobilization with adhesive tape rat-tail；Swimming experiment device is ractangular glass tank (19.4cm × 20.4cm)；3, diamond plate machinery stopwatch, Shanghai Lei Gu Instrument Ltd.；Coulomb array electrochemical high performance liquid chromatograph (ESA company of the U.S.: Model5600A-16 channel detector, Model582solventDeliverySystem, Model542 automatic sampler, CoularrayWin work station)；Dionex-Tcc-100 type column oven (Dai An company of the U.S.)；ThermoD-37520 type High speed refrigerated centrifuge (Heraeus company of Germany)；Phs-25 type pH meter (Shanghai Precision Scientific Apparatus Co., Ltd)；GenPure ultrapure water system (TKA company of Germany)；KQ-500 type ultrasonic cleaner (Kunshan Ultrasonic Instruments Co., Ltd.)；3K super filter tube (PALL company)；BP211D electronic balance (Germany Sartorious)；The quick vortex mixer of Jiamei SK-1 (instrument plant of Jiamei of Community of Jin Tan County city).
1.4 Tail suspension tests (TST)
Take mice 50, be randomly divided into 5 groups, often group 10.It is respectively blank group (normal saline), positive controls (fluoxetine Hydrochloride 4mg/mL) and cefalexin group (80mg/kg), compound (I) group (80mg/kg), cefalexin and compound (I) compositions group [(40mg/kg) cefalexin+(40mg/kg) compound (I)], freely drink water feed 1 time/d of gavage, 0.2mL/ is only, gavage 15d continuously, 1st, 3, 5, after 7 days are administered 1h, mouse tail is sticked fixing at end about 2cm with adhesive plaster, its head is made to hang downwards in upside down shape, from bottom about 5cm.Middle with baffle plate isolation mice sight line.Total inspection 6min, front 2min are adaptive time, motionless (mice aloft stops struggle, or the most tiny limb motion) time of mice in 4min after observation.
1.5 mouse forced swimming test (FST)
Before experiment, 24h carries out swimming instruction 15min, and water, 12h fasting before experiment are can't help in fasting.Swimming test is carried out after within 15th day, being administered 1h.Depth of water 10cm is only put into by single for mice, in the rectangular vessel of water temperature (27 ± 3) DEG C, total inspection 6min, accumulative motionless (floating motionless state in 4min after starting after adapting to 2min to calculate, only exposing nostril to keep breathing, extremity paddling once in a while is unlikely to sink with holding health) time.
2, experimental result
2.1 impacts on the mouse tail suspension dead time
Result is as shown in table 1.The motionless state that mice occurs in outstanding tail model reflects its desperate behavior, administration group antidepressant activity started from the 3rd day to embody, compare with blank group, cefalexin and compound (I) compositions substantially reduce the mouse tail suspension dead time (P < 0.01), and cefalexin group, compound (I) the group mouse tail suspension dead time reduces (P ＜ 0.05).
The table 1 impact (s, x ± s, n=8) on the outstanding tail mice dead time
| Group | 3rd day | 7th day |
| Blank group | 71.11±8.07 | 99.36±9.42 |
| Positive controls | 29.73±3.96 | 40.48±4.16 |
| Cefalexin group | 46.48±4.05 | 57.46±4.30 |
| Compound (I) group | 43.98±4.15 | 52.12±4.02 |
| Cefalexin and compound (I) compositions group | 32.86±3.10 | 43.73±4.37 |
2.2 impacts on the mouse forced swimming test dead time
Result is as shown in table 2.Compare with blank group, cefalexin significantly shortened (P ＜ 0.01) with the dead time of compound (I) compositions group mice swimming, and cefalexin group, compound (I) group mice non-swimming time reduces (P < 0.05).
The table 2 impact (x ± s, n=10) on the mouse forced swimming test dead time
| Group | Dead time/s |
| Blank group | 123.96±12.33 |
| Positive controls | 65.74±8.95 |
| Cefalexin group | 82.35±8.55 |
| Compound (I) group | 89.57±8.70 |
| Cefalexin and compound (I) compositions group | 58.46±6.20 |
Result above shows, cefalexin and compound (I) are respectively provided with obvious antidepressant effect, and both share antidepressant effect and are obviously enhanced, and can develop into antidepressant medicine.
The effect of above-described embodiment indicates that the essentiality content of the present invention, but does not limit protection scope of the present invention with this.It will be understood by those within the art that, technical scheme can be modified or equivalent, without deviating from essence and the protection domain of technical solution of the present invention.
Claims (10)
1. a compound (I) with following structural formula,
2. the pharmaceutical composition of a cefalexin, it is characterised in that: include cefalexin, compound as claimed in claim 1 (I) and pharmaceutically acceptable carrier, be prepared as the dosage form needed.
The pharmaceutical composition of cefalexin the most according to claim 2, it is characterised in that: pharmaceutically acceptable carrier includes diluent, excipient, filler, binding agent, wetting agent, disintegrating agent, absorption enhancer, surfactant, absorption carrier or lubricant.
The pharmaceutical composition of cefalexin the most according to claim 2, it is characterised in that: described dosage form includes tablet, capsule, oral liquid, sucks agent, granule, electuary, pill, powder, unguentum, sublimed preparation, suspensoid, powder, solution, injection, suppository, spray, drop or patch.
5. the preparation method of the compound (I) described in claim 1, it is characterized in that, comprise following operating procedure: Herba Andrographis is pulverized by (a), with 65～85% alcohol heat reflux extract, united extraction liquid, it is concentrated into without alcohol taste, successively with petroleum ether, ethyl acetate and water saturated n-butanol extraction, respectively obtains petroleum ether extract, acetic acid ethyl ester extract and n-butyl alcohol extract；B n-butyl alcohol extract macroporous resin remove impurity in () step (a), first with 8 column volumes of 6% ethanol elution, then with 8 column volumes of 70% ethanol elution, collects 70% eluent, concentrating under reduced pressure obtains 70% ethanol elution concentrate；C in () step (b), 70% ethanol elution concentrate purification on normal-phase silica gel separates, obtain 4 components with the methylene chloride-methanol gradient elution that volume ratio is 50:1,25:1,15:1 and 5:1 successively；D in () step (c), component 4 separates further by purification on normal-phase silica gel, obtain 3 components with the methylene chloride-methanol gradient elution that volume ratio is 10:1,5:1 and 2:1 successively；E reverse phase silica gel that in () step (d), component 2 is bonded by octadecylsilane separates, with the methanol aqueous solution isocratic elution that concentration expressed in percentage by volume is 75%, collecting 8～14 column volume eluents, eluent is concentrated under reduced pressure to give compound (I).
The preparation method of compound the most according to claim 5 (I), it is characterised in that: step (a) is extracted with 75% alcohol heat reflux, united extraction liquid.
The preparation method of compound the most according to claim 5 (I), it is characterised in that: described macroporous resin is AB-8 type macroporous adsorbent resin.
The preparation method of compound the most according to claim 5 (I), it is characterised in that: step (a) replaces ethyl acetate to extract with dichloromethane, obtains dichloromethane extract.
9. the application in the medicine of preparation treatment depression of the compound (I) described in claim 1.
10. the pharmaceutical composition of the arbitrary described cefalexin of claim 2～4 application in the medicine of preparation treatment depression.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106083771A (en) * | 2016-06-13 | 2016-11-09 | 崔坤峰 | The pharmaceutical composition of carbidopa and the medical usage for the treatment of liver cancer thereof |
| CN111826334A (en) * | 2020-07-24 | 2020-10-27 | 暨南大学 | Ultra-long escherichia coli and preparation method and application thereof |
| CN114767690A (en) * | 2022-06-22 | 2022-07-22 | 中国中医科学院中药研究所 | Application of cephalothin acid in preparation of antidepressant drug |
-
2016
- 2016-04-23 CN CN201610258255.7A patent/CN105820053A/en not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106083771A (en) * | 2016-06-13 | 2016-11-09 | 崔坤峰 | The pharmaceutical composition of carbidopa and the medical usage for the treatment of liver cancer thereof |
| CN111826334A (en) * | 2020-07-24 | 2020-10-27 | 暨南大学 | Ultra-long escherichia coli and preparation method and application thereof |
| CN114767690A (en) * | 2022-06-22 | 2022-07-22 | 中国中医科学院中药研究所 | Application of cephalothin acid in preparation of antidepressant drug |
| CN114767690B (en) * | 2022-06-22 | 2022-08-23 | 中国中医科学院中药研究所 | Application of cephalothin acid in preparation of antidepressant drug |
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Application publication date: 20160803 |