CN102002053A - Tetrahydro thienopyridine derivative for treating - Google Patents
Tetrahydro thienopyridine derivative for treating Download PDFInfo
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- CN102002053A CN102002053A CN2009100237730A CN200910023773A CN102002053A CN 102002053 A CN102002053 A CN 102002053A CN 2009100237730 A CN2009100237730 A CN 2009100237730A CN 200910023773 A CN200910023773 A CN 200910023773A CN 102002053 A CN102002053 A CN 102002053A
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- compound
- amino acid
- thienopyridine derivative
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Abstract
The invention provides a novel tetrahydro thienopyridine derivative. The dosage of one or more active compounds in the novel tetrahydro thienopyridine derivative is 0.1-20mg/kg body weight, and the preferable dosage is 0.1-5mg/kg body weight. The novel tetrahydro thienopyridine derivative can be used for producing medicines for preventing and/or treating diseases induced by thrombosis or thromboembolism.
Description
Technical field:
This invention relate to the tetramethylene sulfide that is used for the treatment of and pyridine derivate (especially for prevention and or treatment people's thrombosis bring out/or the thromboembolism disease of bringing out), its application method contains their preparation and their production method.
Technical background:
The vascular disease that comprise myocardial infarction and ishemic stroke are dead and disabled major causes.Though cause that the process of vascular disease is complicated and do not understood fully, the common basic nosetiology of many theories comprise since arteriosclerosis with cause thrombosis or thromboembolism to get plaque rupture.United States Patent (USP) 5288726 discloses thiophane and pyridine derivate can be used for this treatment of diseases, the invention provides a class new tetramethylene sulfide and pyridine derivate.
Summary of the invention:
The object of the present invention is to provide a kind of derivative of this compounds newly.
The object of the present invention is to provide a kind of derivative of this compounds newly.
Its structure is: R
1-O-L,
R
1Expression
The S type
Acyl moiety in the amino acid of L represented amino acid or replacement, wherein preferred amino acids comprises: glycine, L-Ala, Methionin, leucine, Xie Ansuan, phenylalanine, Isoleucine, tryptophane, Serine, Threonine, proline(Pro), methionine(Met), aspartic acid, Histidine, L-glutamic acid, arginine, tyrosine, halfcystine etc.;
L also can represent
The invention provides the production method of above-mentioned formula I compound and pharmaceutical salts thereof: with the esterification of formula II compound,
R
1OH II，
R wherein
1As above-mentioned definition;
Esterification process is: with formula (II) with through the amino acid (as: Boc amino acid, Fmoc amino acid) of overprotection amino, carry out the O-acylation, the preparation intermediate, again intermediate deprotection base is got formula I compound, or formula (II) and acyl chloride reaction prepared intermediate, again the hydrolysis of intermediate water can be got formula I compound, formula I compound is necessary to become acceptable addition salt on the medicine, comprises its subsalt or acid salt; Also can carry out esterification or acylation reaction with hydroxyl, amino, the carboxylic acid of the method for routine and formula I compound generates new derivative the present invention and comprises these derivatives.
Compound of the present invention is useful, because they have pharmacologically active in comprising human animal.Particularly this compound is useful aspect treatment or prevention vascular disease, be applicable to the apoplexy of outbreak in the recent period, myocardial infarction and the patient who makes a definite diagnosis peripheral arterial disease, the generation that can reduce artery congee ocean sclerosis incident is (as myocardium infarct, apoplexy and vascular death), with the acetylsalicylic acid associating, be used for non-ST section and raise impatient property coronary syndrome (unstable angina pectoris or non-Q wave myocardial infarction) patient; The example of the vascular disease that the present invention is contained comprises coronary occlusion, restenosis, acute coronary syndrome, high-risk vascular disease, cerebrovascular aneurysma, congestive heart failure, cardiac alternation, ventricular aneurysm, mural aneurysm, myocardial infarction, asystole, irregular pulse, cardiac edema, cardiac dyspnea, in heart failure, tachycardia, apoplexy, transient ischemic attack, cardiac hemoptysis, incompetence of cardiac valves, heart murmur, disposition is fainted, cardiac tamponade, cerebrovascular disease and/or peripheral arterial disease.
The compounds of this invention can the unit dosage form administration, and route of administration can be enteron aisle or non-enteron aisle, as oral, muscle, subcutaneous, nasal cavity etc.
The The compounds of this invention route of administration can be intravenously administrable.Injection comprises intravenous injection, intramuscular injection, subcutaneous injection and acupoint injection therapy etc.
Form of administration can be pharmaceutically acceptable preparations such as tablet, capsule, dispersible tablet, oral liquid, infusion solutions, little pin, freeze-dried powder.
The compounds of this invention is by the gross weight administration, and its amount is every kg body weight 0.01-40mg, and preferably the consumption of 24h is every kg body weight 0.1-20mg, also can adopt medication several times.
Preferred plan is that the amount that gives one or more active compounds of the present invention once a day is the 0.1-20mg/kg body weight, and preferred dose is the 0.1-5mg/kg body weight.In order to meet people or ideal occlusion regimen for animals, the difference of the visual state of an illness weight of this dosage, treatment difficulty or ease and compound used therefor fluctuates up and down, or follows the doctor's advice.
Below in conjunction with embodiment the present invention is described in further detail, but should understands the non-scope that only limits to these embodiment of scope of the present invention.
Embodiment 1: the preparation of compd A
Reaction equation:
With 2-[2-(hydroxyl)-6,7-dihydro-thiophene also [3,2-c] pyridine-5 (4H)-yl]-1-cyclopropyl-2-(2-fluorophenyl) ethyl ketone 37.3 grams (0.1mol), be dissolved in the 2000ml ethyl acetate, add triphenyl phosphorus 26.3g (0.1mol), BOC-glycine 17.52g (0.1mol), stir and drip diethyl azodiformate (DEAD) 17.42g (0.1mol) room temperature reaction 5h down, filter, feed exsiccant HCl gas in the filtrate to saturated, stirring at room 5h separates out a large amount of white solids, filters, filter cake washs with amount of ethyl acetate, dry compd A hydrochloride 13.8g.
Compound hydrochloride 10g is restrained with after 100 milliliters of dissolved in purified water, slowly dripping saturated sodium carbonate solution is 10 to 10.5 to pH, three each 500ml of usefulness ethyl acetate extraction, united extraction liquid, add anhydrous sodium sulfate drying, evaporated under reduced pressure gets compd A 5g.
Embodiment 2: the R of preparation compd A, S type isomer.
Preparing different according to the method for embodiment 1 is with R type 2-[2-(hydroxyl)-6,7-dihydro-thiophene also [3,2-c] pyridine-5 (4H)-yl]-1-cyclopropyl-2-(2-fluorophenyl) ethyl ketone or S type 2-[2-(hydroxyl)-6,7-dihydro-thiophene also [3,2-c] pyridine-5 (4H)-yl]-1-cyclopropyl-2-(2-fluorophenyl) ethyl ketone replacement 2-[2-(hydroxyl)-6, the 7-dihydro-thiophene is [3,2-c] pyridines-5 (4H)-yl also]-1-cyclopropyl-2-(2-fluorophenyl) ethyl ketone.
Embodiment 3: the preparation of compd B.
With 2-[2-(hydroxyl)-6,7-dihydro-thiophene also [3,2-c] pyridine-5 (4H)-yl]-1-cyclopropyl-2-(2-fluorophenyl) ethyl ketone 37.3 grams (0.1mol), be dissolved in the 2000ml ethyl acetate, add triphenyl phosphorus 26.3g (0.1mol), BOC-L-Ala 18.92g (0.1mol), stir and drip diethyl azodiformate (DEAD) 17.42g (0.1mol) room temperature reaction 5h down, filter, feed exsiccant HCl gas in the filtrate to saturated, stirring at room 5h separates out a large amount of white solids, filters, filter cake washs with amount of ethyl acetate, dry compd B hydrochloride 17.3g.
With after 80 milliliters of dissolved in purified water, slowly dripping saturated sodium carbonate solution is three each 500ml of 10 to 11 usefulness ethyl acetate extraction to pH with compd B hydrochloride 10g gram, and united extraction liquid adds anhydrous sodium sulfate drying, and evaporated under reduced pressure gets compd B 7.1g.
Embodiment 4: the preparation of Compound C
Chemical equation:
With 2-[2-(hydroxyl)-6,7-dihydro-thiophene also [3,2-c] pyridine-5 (4H)-yl]-1-cyclopropyl-2-(2-fluorophenyl) ethyl ketone 37.3 grams (0.1mol), be dissolved in the 2000ml ethyl acetate, the ice bath cooling drips phosphorus oxychloride 30.6 (0.2mol) down, finished room temperature reaction 5 hours, the ice bath cooling slowly adds 50ml distilled water down, stirring reaction 1 hour, and slowly dripping strong caustic accent pH is about 4, evaporate to dryness, the methyl alcohol desalination gets once more evaporate to dryness and gets Compound C 20.8g.
Embodiment 5: the preparation method of compd A hydrochloride sheet
Prescription:
Compd A hydrochloride 100g
Starch 80g
Microcrystalline Cellulose 120g
Magnesium stearate 2.0g
Vltra tears (E-30) (4% solution) is an amount of
Make 1000
Method for making: prepare 4% Vltra tears (E-30) solution, standby.Taking by weighing 20g starch, to put 105 ℃ of dryings 5 hours standby.Take by weighing compd A hydrochloride, the Microcrystalline Cellulose of 60g starch and recipe quantity, mixing was pulverized 80 mesh sieves., granulate with 20 mesh sieves, material system softwood with 4% Vltra tears (E-30) solution in 50-60 ℃ of moisture content about 3% that is dried in the particle.Cross the whole grain of 20 mesh sieves, add dry starch (105 ℃ drying 5 hours), the magnesium stearate of recipe quantity, mix eventually, survey intermediate content, stator is heavy; Compressing tablet.
Claims (3)
1. hydroxyl, amino, the carboxylic moiety in the compound of general formula (I) or its hydrate or their pharmaceutical salts and their structural formula carried out the derivative of esterification or acylation reaction generation:
R
1-O-L (I)
R
1Expression
The S type,
The R type.Acyl moiety in acyl moiety in the L represented amino acid, the amino acid of replacement or
2. a medicinal compositions is characterized in that, contain the treatment effective dose according to claim 1 compound as activeconstituents and pharmaceutically acceptable carrier.
3. according to the purposes of the described pharmaceutical composition of claim 3, be used to produce the thrombosis that prevents and/or treats people medicine that bring out or the disease that thromboembolism is brought out.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN2009100237730A CN102002053A (en) | 2009-09-02 | 2009-09-02 | Tetrahydro thienopyridine derivative for treating |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100237730A CN102002053A (en) | 2009-09-02 | 2009-09-02 | Tetrahydro thienopyridine derivative for treating |
Publications (1)
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| CN2009100237730A Pending CN102002053A (en) | 2009-09-02 | 2009-09-02 | Tetrahydro thienopyridine derivative for treating |
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