CN107011380A - A kind of diphosphonic acid derivative and containing diphosphonic acid derivative composition treatment fracture application - Google Patents
A kind of diphosphonic acid derivative and containing diphosphonic acid derivative composition treatment fracture application Download PDFInfo
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- CN107011380A CN107011380A CN201610057102.6A CN201610057102A CN107011380A CN 107011380 A CN107011380 A CN 107011380A CN 201610057102 A CN201610057102 A CN 201610057102A CN 107011380 A CN107011380 A CN 107011380A
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- acid derivative
- diphosphonic acid
- fracture
- composition
- treatment
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- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical class OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims abstract description 16
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 229920001353 Dextrin Polymers 0.000 claims description 5
- 239000004375 Dextrin Substances 0.000 claims description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 5
- 229920002472 Starch Polymers 0.000 claims description 5
- 235000011132 calcium sulphate Nutrition 0.000 claims description 5
- 235000019425 dextrin Nutrition 0.000 claims description 5
- 239000008101 lactose Substances 0.000 claims description 5
- 235000019698 starch Nutrition 0.000 claims description 5
- 239000008107 starch Substances 0.000 claims description 5
- 235000019359 magnesium stearate Nutrition 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims description 3
- 235000019799 monosodium phosphate Nutrition 0.000 claims description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 3
- 229940079827 sodium hydrogen sulfite Drugs 0.000 claims description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 235000001727 glucose Nutrition 0.000 claims description 2
- 239000007935 oral tablet Substances 0.000 claims description 2
- 229940096978 oral tablet Drugs 0.000 claims description 2
- 239000008213 purified water Substances 0.000 claims description 2
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims 2
- DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 claims 1
- JJJOZVFVARQUJV-UHFFFAOYSA-N 2-ethylhexylphosphonic acid Chemical compound CCCCC(CC)CP(O)(O)=O JJJOZVFVARQUJV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 235000009508 confectionery Nutrition 0.000 claims 1
- 239000003292 glue Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 10
- 238000009940 knitting Methods 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 6
- 210000000988 bone and bone Anatomy 0.000 abstract description 5
- 108010048734 sclerotin Proteins 0.000 abstract description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 abstract description 2
- 235000019738 Limestone Nutrition 0.000 abstract description 2
- 230000006907 apoptotic process Effects 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000037182 bone density Effects 0.000 abstract description 2
- 229910001424 calcium ion Inorganic materials 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 abstract description 2
- 239000013522 chelant Substances 0.000 abstract description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 2
- 239000006028 limestone Substances 0.000 abstract description 2
- 239000011707 mineral Substances 0.000 abstract description 2
- 210000002997 osteoclast Anatomy 0.000 abstract description 2
- RYIOLWQRQXDECZ-UHFFFAOYSA-N phosphinous acid Chemical compound PO RYIOLWQRQXDECZ-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000630 rising effect Effects 0.000 abstract description 2
- 206010017076 Fracture Diseases 0.000 description 23
- 208000010392 Bone Fractures Diseases 0.000 description 22
- 230000037396 body weight Effects 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 230000006378 damage Effects 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 208000020084 Bone disease Diseases 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 210000003414 extremity Anatomy 0.000 description 2
- 210000002082 fibula Anatomy 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 206010010214 Compression fracture Diseases 0.000 description 1
- 208000012661 Dyskinesia Diseases 0.000 description 1
- 206010014080 Ecchymosis Diseases 0.000 description 1
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000032912 Local swelling Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001399 anti-metabolic effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000001699 lower leg Anatomy 0.000 description 1
- 210000004705 lumbosacral region Anatomy 0.000 description 1
- 210000001872 metatarsal bone Anatomy 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- WRUUGTRCQOWXEG-UHFFFAOYSA-N pamidronate Chemical compound NCCC(O)(P(O)(O)=O)P(O)(O)=O WRUUGTRCQOWXEG-UHFFFAOYSA-N 0.000 description 1
- 229960003978 pamidronic acid Drugs 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 210000002303 tibia Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/60—Quinoline or hydrogenated quinoline ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to a kind of diphosphonic acid derivative and the composition treatment containing diphosphonic acid derivative fracture application.The structural formula of such diphosphonic acid derivative shown in formula I, wherein R1For O (CH2)-A, A is imidazole ring or quinoline ring；R2For hydroxyl or chlorine.The diphosphonic acid derivative of the present invention is used as a kind of medicine of fracture, can be in high-affinity with the hydroxyl phosphine lime stone in sclerotin, the apoptosis that bone mineral surface promotes osteoclast is adsorbed in calcium ion formation chelate, the rising in value of Gegenbaur's cell is stimulated, ripe, so that bone density increase.To the facilitation of knitting substantially, treatment cycle is short, and Small side effects, cost is low, suitable for clinical expansion for the diphosphonic acid derivative and composition containing diphosphonic acid derivative.
Description
Technical field
The present invention relates to diphosphonic acid derivative and the composition treatment containing diphosphonic acid derivative fracture application.
Background technology
Fracture be due to the reasons such as wound or pathology with causing bone parts or a kind of disease for being fully broken.Its main clinical manifestation is：Fractures have a localized pain and tenderness, local swelling and ecchymosis occur, limb function position or completely lose, and cacomelia and abnormal movement still occurs in completeness sclerotin.More than one piece of fracturing also happens occasionally in children and old man, the young and the middle aged.The main cause fractured has three kinds of situations：(1) direct violence, violence directly acts on a certain position of bone and causes the portion to fracture, then injury is fractured, and is often accompanied by different degrees of soft tissue destruction, and such as wheel hits shank, fracture of shaft of tibia and fibula occurs at shock；(2) indirect violence, distant place is set to fracture by longitudinal conduction, leverage or twisting action when indirect violence is acted on, when such as falling foot from eminence and landing, trunk is because gravity relationship is drastically to pre-buckling, and by the effect of jack knife power compression fracture is occurred for chest lumbar spine intersection centrum；(3) accumulation property strain, direct or indirect damage long-term, repeatedly, slight can cause a certain privileged site fracture of limbs, and such as remote march easily causes 1/3 shaft fracture under second and third metatarsal and fibula.
Clinically treatment fracture it is main using manual reset, it is fixed after clear-cutting forestland, be aided with the anti-inflammatory for avoiding inflammation from occurring and promote knitting again in addition and knitting promote medicine.And it is mostly Chinese medicine preparation promoting blood circulation and removing blood stasis that the knitting used at present, which promotes medicine, healing time is longer, and therapeutic effect is not good enough, and huge painful and inconvenience is caused to patient, has a strong impact on the daily life of patient.
Diphosphonic acid derivative class medicine is the kind new medicine of antimetabolic osteopathy of growing up in recent years, for treating many bone diseases.Such as Etidronic Acid, Allan phosphoric acid, pamidronic acid etc., they are all the medicines of good treatment fracture, and result of study shows：Preferably, such medicine can be effectively promoted bone generation to the two banks drug effect of nitrogenous two banks or side chain containing heterocycle containing amino, increase skeleton density, so as to play therapeutic action.
The content of the invention
It is an object of the invention to provide a kind of diphosphonic acid derivative and the fracture of the composition treatment containing diphosphonic acid derivative application, such medicine can promote knitting, effectively shorten healing time.
The diphosphonic acid derivative that the present invention is provided, its structure is shown in formula I：
In the Formulas I, R1For O (CH2)-A, wherein A is imidazole ring or quinoline ring；R2For hydroxyl or chlorine.
Diphosphonic acid derivative provided by the present invention is selected from any one following compound：
C1：R1=O (CH2)-A, A is imidazole ring；R2=OH；
C2：R1=O (CH2)-A, A is imidazole ring；R2=Cl；
C3：R1=O (CH2)-A, A is quinoline ring；R2=OH；
C4：R1=O (CH2)-A, A is quinoline ring；R2=Cl.
The present invention also provides applications of the described diphosphonic acid derivative C1-C4 in treatment fracture.
A kind of composition containing diphosphonic acid derivative that the present invention is provided, said composition diphosphonic acid derivative and auxiliary material shown in Formulas I are constituted, and the auxiliary material is selected from lactose, glucose, starch, dextrin, calcium sulfate, magnesium stearate, purified water, ethanol (≤50%), glycerine (≤50%), sodium dihydrogen phosphate, glycine, sodium hydrogensulfite.
The present invention also provides application of the composition containing diphosphonic acid derivative in treatment fracture.
Further, the composition can be made into injection-type or oral tablet, capsule.
The diphosphonic acid derivative of the present invention is used as a kind of medicine of fracture, can be in high-affinity with the hydroxyl phosphine lime stone in sclerotin, the apoptosis that bone mineral surface promotes osteoclast is adsorbed in calcium ion formation chelate, stimulate the rising in value of Gegenbaur's cell, it is ripe so that bone density increase, knitting facilitation is obvious, treatment cycle is short, Small side effects, cost is low, suitable for clinical expansion.
Embodiment
The method of the present invention is illustrated below by specific embodiment, but the invention is not limited in this.
Embodiment 1：
Diphosphonic acid derivative C1 and lactose, dextrin, starch, calcium sulfate be made tablet be used for treat fracture example, arm completeness fracture patient 40, female 24 in all patients is male 16；Year ridge 15-68 Sui.All patients are randomly divided into experimental group (21) and control group (19).The sex of two groups of patients, age have comparativity without statistical meaning.The mg/kg body weight/day of oral agents consumption active principle 0.05 of the present invention is to 5 mg/kg body weight/days, preferably 0.1 mg/kg body weight/day to 1 mg/kg body weight/day, and experimental group preferably comprises effect component 1,2,5,10 milligrams of oral agents, oral agents consumption is adjusted according to symptom.4 weeks experimental periods, the obvious knitting of check in 2-3 weeks is effective for data.Final statistical experiment group effective percentage 86%, control group effective percentage is 37%.
Embodiment 2：
Diphosphonic acid derivative C2 and lactose, dextrin, starch, calcium sulfate, magnesium stearate be made tablet be used for treat fracture example, arm completeness fracture patient 40, female 17 in all patients is male 23；Year ridge 15-65 Sui.All patients are randomly divided into experimental group (22) and control group (18).The sex of two groups of patients, age have comparativity without statistical meaning.The mg/kg body weight/day of oral agents consumption active principle 0.05 of the present invention is to 5 mg/kg body weight/days, preferably 0.1 mg/kg body weight/day to 1 mg/kg body weight/day, and experimental group preferably comprises effect component 1,2,5,10 milligrams of oral agents, oral agents consumption is adjusted according to symptom.4 weeks experimental periods, the obvious knitting of check in 2-3 weeks is effective for data.Final statistical experiment group effective percentage 91%, control group effective percentage is 39%.
Embodiment 3：
Diphosphonic acid derivative C3 and lactose, dextrin, starch, calcium sulfate, magnesium stearate be made tablet be used for treat fracture example, arm completeness fracture patient 41, female 23 in all patients is male 18；Year ridge 15-65 Sui.All patients are randomly divided into experimental group (22) and control group (19).The sex of two groups of patients, age have comparativity without statistical meaning.The mg/kg body weight/day of oral agents consumption active principle 0.05 of the present invention is to 5 mg/kg body weight/days, preferably 0.1 mg/kg body weight/day to 1 mg/kg body weight/day, and experimental group preferably comprises effect component 1,2,5,10 milligrams of oral agents, oral agents consumption is adjusted according to symptom.4 weeks experimental periods, the obvious knitting of check in 2-3 weeks is effective for data.Final statistical experiment group effective percentage 86%, control group effective percentage is 47%.
Embodiment 4
Diphosphonic acid derivative C4 and pure water, glucose, ethanol, sodium dihydrogen phosphate, glycine, glycerine, sodium hydrogensulfite be made injection be used for treat fracture example, arm completeness fracture patient 43, female 23 in all patients is male 20；Age 13-71 Sui.All patients are randomly divided into experimental group (22) and control group (21).The sex of two groups of patients, age have comparativity without statistical meaning.Injection consumption of the present invention, the mg/kg body weight of dosage 0.05/hour to 5 mg/kg body weight/hour during continuous transfusion, it is preferred that 0.1 mg/kg body weight/hour to 2 mg/kg body weight/hour, 4 weeks experimental periods, the obvious knitting of check in 2-3 weeks is effective for data.Final statistical experiment group effective percentage 91%, control group effective percentage is 38%.
Claims (6)
1. diphosphonic acid derivative shown in Formulas I：
In the Formulas I, R1For O (CH2)-A, wherein A is imidazole ring or quinoline ring；R2
For hydroxyl or chlorine.
2. diphosphonic acid derivative according to claim 1, it is characterised in that：The diphosphine
Acid derivative is selected from any one following compound：
C1：R1=O (CH2)-A, A is imidazole ring；R2=OH；
C2：R1=O (CH2)-A, A is imidazole ring；R2=Cl；
C3：R1=O (CH2)-A, A is quinoline ring；R2=OH；
C4：R1=O (CH2)-A, A is quinoline ring；R2=Cl.
3. application of the diphosphonic acid derivative in treatment fracture described in claim 2.
4. a kind of composition containing diphosphonic acid derivative, said composition di 2 ethylhexyl phosphonic acid as shown in Formulas I spreads out
Biological and auxiliary material composition, the auxiliary material be selected from lactose, glucose, starch, dextrin, calcium sulfate,
It is magnesium stearate, purified water, ethanol (≤50%), glycerine (≤50%), sodium dihydrogen phosphate, sweet
Propylhomoserin, sodium hydrogensulfite.
5. the composition containing diphosphonic acid derivative described in claim 4 is in treatment fracture
Using.
6. the composition according to claim 5 containing diphosphonic acid derivative is fractured in treatment
In application, it is characterised in that：The composition can be made into injection-type or oral tablet, glue
Capsule.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610057102.6A CN107011380A (en) | 2016-01-28 | 2016-01-28 | A kind of diphosphonic acid derivative and containing diphosphonic acid derivative composition treatment fracture application |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610057102.6A CN107011380A (en) | 2016-01-28 | 2016-01-28 | A kind of diphosphonic acid derivative and containing diphosphonic acid derivative composition treatment fracture application |
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| CN107011380A true CN107011380A (en) | 2017-08-04 |
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Application publication date: 20170804 |