CN104557929B - One class contains coagulation factor xa inhibitors and the purposes thereof of bicyclic amide structure - Google Patents
One class contains coagulation factor xa inhibitors and the purposes thereof of bicyclic amide structure Download PDFInfo
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- CN104557929B CN104557929B CN201510083411.6A CN201510083411A CN104557929B CN 104557929 B CN104557929 B CN 104557929B CN 201510083411 A CN201510083411 A CN 201510083411A CN 104557929 B CN104557929 B CN 104557929B
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- 0 *C(CCC1)C[C@]2[C@@]1(N)NCCC2 Chemical compound *C(CCC1)C[C@]2[C@@]1(N)NCCC2 0.000 description 4
- JDCNIUJWLNZLIY-ZJUUUORDSA-N O=C(c1ccc[s]1)N1[C@@H](CNC2)[C@@H]2CCC1 Chemical compound O=C(c1ccc[s]1)N1[C@@H](CNC2)[C@@H]2CCC1 JDCNIUJWLNZLIY-ZJUUUORDSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Abstract
The present invention relates to the pharmaceutical field relevant to phlebothrombosis disease. Specifically, the present invention relates to a class containing the FXa inhibitor of two ring hydrazide structure, its preparation method and the application in preparation phlebothrombosis disease medicament.Wherein, R is selected from C1-C3Alkyl.
Description
Technical field
The present invention relates to the pharmaceutical field of phlebothrombosis disease treatment. More particularly, the present invention relates to the class that phlebothrombosis disease is had therapeutic action containing the FXa inhibitor of bicyclic amide structure, its preparation method, and the purposes in pharmacy.
Background technology
The deterioration of clotting ability is the important factor of unstable angina pectoris, brain osmanthus plug, cerebral embolism, cardiac muscle thrombosis when proposing the inaccessible again or extracorporeal circulation after the thrombosis after plug, lung infraction, pulmonary infarction, thromboangiitis obliterans, venous thrombosis, disseminated intravascular coagulation, replacing valve, revascularization. In Arterial system, abnormal thrombus is formed main relevant with coronary artery, the cerebrovascular and peripheral blood vessel, close that relevant disease mainly comprises that Acute Myocardial Infarction (AMI), instability stenocardia, thromboembolism and the thromboembolism treatment acute vascular relevant with percutaneous coronary artery angiography intracavity forming operation (PTCA) closes with the thrombosis of these blood vessels, transient ischemic attack, apoplexy, intermittent claudication and coronary artery bypass graft surgery (CABG) or peripheral arterial bypass graft. For vein blood vessel, pathologic thrombosis often occurs in the veins of lower extremity after belly, knee joint and Hip operation (venous thrombosis, DVT). DVT also makes patient be among the highly dangerous easily suffering from pulmonary thromboembolism. So, it is necessary to developing excellent anti-coagulant, this kind of anti-coagulant has excellent dose response, time length length, hemorrhage dangerous little, is almost free from side effects, and namely uses and oral also can reach abundant effect very soon.
Research according to the mechanism of action to various anti-coagulant, coagulation factor xa inhibitors (FXa inhibitor) is considered as good anti-coagulant. Factor Xa is second from the bottom kind of enzyme in blood coagulation chain. The restraining effect of factor Xa obtains by directly forming complex body between this inhibitor and enzyme, and therefore this enzyme is unrelated with blood plasma cofactor Antithrombin III. Effective factor Xa restraining effect is used this compound by oral administration, venoclysis continuously, quick dense note intravenously administrable or any other parenteral route approach and is realized, and thus can obtain the required effect stoping factor Xa to bring out thrombogen formation zymoplasm. Another advantage of FXa inhibitor be the effective dose in thrombotic model and in experimental hemorrhage model the dosage of time expand have very big difference. By this this test-results, it is possible to think that FXa inhibitor is the anti-coagulant that hemorrhage risk is less. Report the multiple compound being used as FXa inhibitor, and had and many ratify clinically, such as razaxaban etc.
The present invention discloses the FXa inhibitor containing two ring hydrazide structure of a class formation novelty, and these compounds can be used for preparing the medicine for the treatment of phlebothrombosis disease.
Summary of the invention
It is an object of the present invention to provide the FXa inhibitor of a kind of excellent activity with general formula I.
It is a further object to provide the method that preparation has the compound of general formula I.
It is also another object of the present invention to provide the compound containing general formula I as effective constituent, and the medicinal compositions of one or more pharmaceutically acceptable carriers, vehicle or thinner, and the application in treatment phlebothrombosis disease. Now content of the present invention is specifically described by object in conjunction with the present invention.
The compound that the present invention has general formula (I) has following structural formula:
Wherein, R is selected from C1-C3Alkyl.
More preferably the compound of general formula (I) has following structure,
General formula of the present invention (I) compound is synthesized by following route:
Compound I I reacts with triphenylmethyl chloride (TrCl) in the presence of a base, obtains compound III; There is lower and compound IV condensation in compound III, obtain compound V at DCC (N, N'-dicyclohexyl carbodiimide); Trityl is sloughed in compound V acid treatment, obtains compound VI; Compound VI DCC exist under with compound VI I condensation, obtain Compound I; Wherein, the definition of R is as previously mentioned. Initial compounds II can refer to US5468742 (1995) and obtains.
Compound of Formula I of the present invention has the restraining effect of FXa, can be used as effective constituent for the preparation of phlebothrombosis medicine. The activity of compound of Formula I of the present invention is verified by receptor binding assays.
The compound of Formula I of the present invention is effective in quite wide dosage range. The dosage that such as every day takes, within the scope of 1mg-1000mg/ people, is divided into once or administration for several times. The actual dosage taking compound of Formula I of the present invention can be determined according to relevant situation by doctor.
Embodiment
Below in conjunction with embodiment, the present invention is further illustrated. It should be noted that, following embodiment be only for illustration of, and not for limiting the present invention. Those skilled in the art all should within the protection domain required by the application's claim according to the various changes that the teachings of the present invention is made.
The synthesis of embodiment 1 Compound I-1
A. the synthesis of compound III
Compound I I (1.26g, 10mmol) and triethylamine (3.04g, 30mmol) are dissolved in the DMF of 10mL drying, and ice-water bath cooling is lower stirs, and slowly drips and adds by Triphenyl methane chloride 99 (TrCl; 3.07g, 11mmol) and 10mL drying DMF preparation solution. After dropwising, gained reaction mixture at room temperature stirs 3 hours, and TLC shows reaction to be completed. Reaction mixture pours in 120mL frozen water, CH2Cl2(50mL �� 3) extract, and merge extraction phase, use salt water washing, anhydrous sodium sulfate drying. Taking out and filter siccative, filtrate is steamed dry on a rotary evaporator, and the resistates obtained uses column chromatography purification, obtains compound III, white solid, ESI-MS, m/z=369 ([M+H]+)��
B. the synthesis of compound V-1
Compound III (2.21g, 6mmol) and compound IV-1 (0.95g, 6mmol) are dissolved in the THF of 20mL drying, stirred at ambient temperature, add DCC (1.65g, 8mmol) and DMAP (DMAP; 0.5g), then room temperature for overnight, TLC detection reaction completes. Reaction mixture pours in 120mL frozen water, CH2Cl2(50mL �� 3) extract, and merge extraction phase, successively with 3% dilute hydrochloric acid and salt water washing, and anhydrous sodium sulfate drying. Taking out and filter siccative, filtrate is steamed dry on a rotary evaporator, and the resistates obtained uses column chromatography purification, obtains compound V-1, white-yellowish solid, ESI-MS, m/z=510 ([M+H]+)��
C. the synthesis of compound VI-1
Compound V-1 (2.55g, 5mmol) is dissolved in 20mL methyl alcohol, and stirred at ambient temperature adds 1mL concentrated hydrochloric acid, continues to stir 5 hours under room temperature, and TLC checks and finds that reaction completes. Reaction mixture pours in 120mL frozen water, with saturated NaHCO3Solution regulates pH=8, CH2Cl2(50mL �� 3) extract, and merge extraction phase, use salt water washing, anhydrous sodium sulfate drying. Taking out and filter siccative, filtrate is steamed dry on a rotary evaporator, and the resistates obtained uses column chromatography purification, obtains compound VI-1, white solid, ESI-MS, m/z=267 ([M+H]+)��
D. the synthesis of Compound I-1
Compound VI-1 (0.53g, 2mmol) and compound VI I-1 (0.28g, 2mmol) are dissolved in the THF of 8mL drying, stirred at ambient temperature, add DCC (0.62g, 3mmol) and DMAP (DMAP; 0.1g), then room temperature for overnight, TLC detection reaction completes. Reaction mixture pours in 100mL frozen water, CH2Cl2(50mL �� 3) extract, and merge extraction phase, successively with 3% dilute hydrochloric acid and salt water washing, and anhydrous sodium sulfate drying. Taking out and filter siccative, filtrate is steamed dry on a rotary evaporator, and the resistates obtained uses column chromatography purification, obtains Compound I-1, white solid, ESI-MS, m/z=391 ([M+H]+)��
The synthesis of embodiment 2 Compound I-2
A. the synthesis of compound III
Compound I I (1.26g, 10mmol) and triethylamine (3.04g, 30mmol) are dissolved in the DMF of 10mL drying, and ice-water bath cooling is lower stirs, and slowly drips and adds by Triphenyl methane chloride 99 (TrCl; 3.07g, 11mmol) and 10mL drying DMF preparation solution. After dropwising, gained reaction mixture at room temperature stirs 3 hours, and TLC shows reaction to be completed. Reaction mixture pours in 120mL frozen water, CH2Cl2(50mL �� 3) extract, and merge extraction phase, use salt water washing, anhydrous sodium sulfate drying. Taking out and filter siccative, filtrate is steamed dry on a rotary evaporator, and the resistates obtained uses column chromatography purification, obtains compound III, white solid, ESI-MS, m/z=369 ([M+H]+)��
B. the synthesis of compound V-2
Compound III (2.21g, 6mmol) and compound IV-2 (1.03g, 6mmol) are dissolved in the THF of 20mL drying, stirred at ambient temperature, add DCC (1.65g, 8mmol) and DMAP (DMAP; 0.5g), then room temperature for overnight, TLC detection reaction completes. Reaction mixture pours in 120mL frozen water, CH2Cl2(50mL �� 3) extract, and merge extraction phase, successively with 3% dilute hydrochloric acid and salt water washing, and anhydrous sodium sulfate drying. Taking out and filter siccative, filtrate is steamed dry on a rotary evaporator, and the resistates obtained uses column chromatography purification, obtains compound V-2, white-yellowish solid, ESI-MS, m/z=522 ([M+H]+)��
C. the synthesis of compound VI-2
Compound V-2 (2.61g, 5mmol) is dissolved in 20mL methyl alcohol, and stirred at ambient temperature adds 1mL concentrated hydrochloric acid, continues to stir 5 hours under room temperature, and TLC checks and finds that reaction completes. Reaction mixture pours in 120mL frozen water, with saturated NaHCO3Solution regulates pH=8, CH2Cl2(50mL �� 3) extract, and merge extraction phase, use salt water washing, anhydrous sodium sulfate drying. Taking out and filter siccative, filtrate is steamed dry on a rotary evaporator, and the resistates obtained uses column chromatography purification, obtains compound VI-2, white solid, ESI-MS, m/z=281 ([M+H]+)��
D. the synthesis of Compound I-2
Compound VI-2 (0.56g, 2mmol) and compound VI I-1 (0.28g, 2mmol) are dissolved in the THF of 8mL drying, stirred at ambient temperature, add DCC (0.62g, 3mmol) and DMAP (DMAP; 0.1g), then room temperature for overnight, TLC detection reaction completes. Reaction mixture pours in 100mL frozen water, CH2Cl2(50mL �� 3) extract, and merge extraction phase, successively with 3% dilute hydrochloric acid and salt water washing, and anhydrous sodium sulfate drying. Taking out and filter siccative, filtrate is steamed dry on a rotary evaporator, and the resistates obtained uses column chromatography purification, obtains Compound I-2, white solid, ESI-MS, m/z=405 ([M+H]+)��
The synthesis of embodiment 3 reference compound D-1
Compound D-1 is all the compound (not yet open) that the present inventor designs in research process.
A. the synthesis of compound III
Compound I I (1.26g, 10mmol) and triethylamine (3.04g, 30mmol) are dissolved in the DMF of 10mL drying, and ice-water bath cooling is lower stirs, and slowly drips and adds by Triphenyl methane chloride 99 (TrCl; 3.07g, 11mmol) and 10mL drying DMF preparation solution. After dropwising, gained reaction mixture at room temperature stirs 3 hours, and TLC shows reaction to be completed. Reaction mixture pours in 120mL frozen water, CH2Cl2(50mL �� 3) extract, and merge extraction phase, use salt water washing, anhydrous sodium sulfate drying. Taking out and filter siccative, filtrate is steamed dry on a rotary evaporator, and the resistates obtained uses column chromatography purification, obtains compound III, white solid, ESI-MS, m/z=369 ([M+H]+)��
B. the synthesis of compound V-3
Compound III (2.21g, 6mmol) and compound IV-2 (0.77g, 6mmol) are dissolved in the THF of 20mL drying, stirred at ambient temperature, add DCC (1.65g, 8mmol) and DMAP (DMAP; 0.5g), then room temperature for overnight, TLC detection reaction completes. Reaction mixture pours in 120mL frozen water, CH2Cl2(50mL �� 3) extract, and merge extraction phase, successively with 3% dilute hydrochloric acid and salt water washing, and anhydrous sodium sulfate drying. Taking out and filter siccative, filtrate is steamed dry on a rotary evaporator, and the resistates obtained uses column chromatography purification, obtains compound V-3, white solid, ESI-MS, m/z=479 ([M+H]+)��
C. the synthesis of compound VI-3
Compound V-3 (2.40g, 5mmol) is dissolved in 20mL methyl alcohol, and stirred at ambient temperature adds 1mL concentrated hydrochloric acid, continues to stir 5 hours under room temperature, and TLC checks and finds that reaction completes. Reaction mixture pours in 120mL frozen water, with saturated NaHCO3Solution regulates pH=8, CH2Cl2(50mL �� 3) extract, and merge extraction phase, use salt water washing, anhydrous sodium sulfate drying. Taking out and filter siccative, filtrate is steamed dry on a rotary evaporator, and the resistates obtained uses column chromatography purification, obtains compound VI-3, white solid, ESI-MS, m/z=237 ([M+H]+)��
D. the synthesis of Compound D-1
Compound VI-3 (0.47g, 2mmol) and compound VI I-1 (0.28g, 2mmol) are dissolved in the THF of 8mL drying, stirred at ambient temperature, add DCC (0.62g, 3mmol) and DMAP (DMAP; 0.1g), then room temperature for overnight, TLC detection reaction completes. Reaction mixture pours in 100mL frozen water, CH2Cl2(50mL �� 3) extract, and merge extraction phase, successively with 3% dilute hydrochloric acid and salt water washing, and anhydrous sodium sulfate drying. Taking out and filter siccative, filtrate is steamed dry on a rotary evaporator, and the resistates obtained uses column chromatography purification, obtains Compound D-1, white solid, ESI-MS, m/z=360 ([M+H]+)��
The external inhibition test to FXa of embodiment 4 compound
By the 5%DMSO solution (10 �� L) (its concentration progressively suitably sets) of embodiment compound to be measured and positive drug EDOXABAN, Tris damping fluid (100mMTris, 200mM Repone K, 0.2%BSA, pH7.4) (40 �� l) and 0.0625U/mL people FXa (EnzymeResearchLabolatories, Inc., dissolve with Tris damping fluid and dilute the hole that (10 �� l) puts into 96 hole minitype plates respectively, add 750 ��Ms of aqueous solution (40 �� l) of S2222 (ChromogenixCo.), to measure under 10 minutes room temperatures the absorbancy at 405nm, thus measure absorbancy and increase (�� OD/min). as negative control, replace test compound with Tris damping fluid.
According to formula below, on the ordinate zou that the percent inhibition (%) when test compound initial concentration and test compound final concn is painted on the orthogonal probability tables of logarithm respectively and X-coordinate, to determine 50% suppression dosage (IC50Value).
Percent inhibition (%)=[1-(the �� OD/min of sample)/(comparison �� OD/min)] �� 100
Test result sees the following form.
| Compound | IC50(nM) |
| Edoxaban | 3.9 |
| Reference compound D-1 | 6.5 |
| The compounds of this invention I-1 | 3.6 |
| The compounds of this invention I-2 | 4.3 |
From upper table result it may be seen that the compound of the present invention is good FXa inhibitor, it is possible to as the medicine of preparation treatment phlebothrombosis disease.
Claims (3)
1. following compounds:
2. synthesize the method for compound described in claim 1:
Compound I I reacts with triphenylmethyl chloride (TrCl) in the presence of a base, obtains compound III; Compound III DCC exist under with compound IV condensation, obtain compound V; Trityl is sloughed in compound V acid treatment, obtains compound VI; Compound VI DCC exist under with compound VI I condensation, obtain Compound I; Wherein, R is selected from methyl, ethyl.
3. compound described in claim 1 treats the application in phlebothrombosis disease medicament in preparation.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1420882A (en) * | 1999-07-28 | 2003-05-28 | 阿温蒂斯药物公司 | Substd. oxoazaheterocyclyl compounds |
| CN101309919A (en) * | 2005-11-16 | 2008-11-19 | 弗·哈夫曼-拉罗切有限公司 | Novel pyrrolidine derivatives as inhibitors of coagulation factor XA |
| CN103242310A (en) * | 2012-02-10 | 2013-08-14 | 苏州迈泰生物技术有限公司 | Pyrazolo pyridone compound and its application in preparation of anticoagulant |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2493875B1 (en) * | 2009-10-27 | 2014-08-06 | Boehringer Ingelheim International GmbH | Heterocyclic compounds as ccr1 receptor antagonists |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1420882A (en) * | 1999-07-28 | 2003-05-28 | 阿温蒂斯药物公司 | Substd. oxoazaheterocyclyl compounds |
| CN101309919A (en) * | 2005-11-16 | 2008-11-19 | 弗·哈夫曼-拉罗切有限公司 | Novel pyrrolidine derivatives as inhibitors of coagulation factor XA |
| CN103242310A (en) * | 2012-02-10 | 2013-08-14 | 苏州迈泰生物技术有限公司 | Pyrazolo pyridone compound and its application in preparation of anticoagulant |
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