Nothing Special   »   [go: up one dir, main page]

CN103242310A - Pyrazolo pyridone compound and its application in preparation of anticoagulant - Google Patents

Pyrazolo pyridone compound and its application in preparation of anticoagulant Download PDF

Info

Publication number
CN103242310A
CN103242310A CN2012100297451A CN201210029745A CN103242310A CN 103242310 A CN103242310 A CN 103242310A CN 2012100297451 A CN2012100297451 A CN 2012100297451A CN 201210029745 A CN201210029745 A CN 201210029745A CN 103242310 A CN103242310 A CN 103242310A
Authority
CN
China
Prior art keywords
compound
prodrug
bolites
meta
hydrate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN2012100297451A
Other languages
Chinese (zh)
Inventor
殷建明
朱惠霖
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
METABOMICS Inc
Original Assignee
METABOMICS Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by METABOMICS Inc filed Critical METABOMICS Inc
Priority to CN2012100297451A priority Critical patent/CN103242310A/en
Publication of CN103242310A publication Critical patent/CN103242310A/en
Pending legal-status Critical Current

Links

Landscapes

  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention relates to a novel pyrazolo pyridone compound and its application in the preparation of an anticoagulant. The pyrazolo pyridone compound is an ideal direct blood coagulation factor Xa inhibitor and can be used for preventing or treating thrombosis or other indications including auricular fibrillation, acute coronary artery syndrome, acute symptomatic venous thrombosis, cerebral arterial thrombosis and the like. The compound provided by the invention has advantages of less first pass effect, high effective bioavailability and less side-effect. When the compound is used in treating an indication related to the function of direct blood coagulation factor Xa, the compound has advantages of little dosage and little side-effect.

Description

Pyrazolopyridine ketone compounds and the purposes in preparing anticoagulation medicine thereof
Technical field
The present invention relates to the Pyrazolopyridine ketone compounds and prevent and/or treat the purposes in anticoagulation medicine in preparation.
Background technology
Along with the variation of human lives's Working environment, the incidence of thrombotic diseases is just at increase year after year, the disease that myocardial infarction and cerebral infarction are respectively current lethality rates, disability rate is the highest.Along with the aging of population, the increase of cardiovascular disease incidence rate, the demand of anticoagulant is constantly increased, wish that novel anticoagulation medicine will bring more benefits to the patient.
In various thrombin, Xa factor is arranged in the key position of blood coagulation waterfall.Xa factor is the point of endogenous and exogenous cruor pathway, and the catalysis thrombogen changes zymoplasm into.Effect by suppressing Xa factor can Trombin inhibiting generation, thereby affect the coagulation process of thrombin-mediated.Zymoplasm has vital role in coagulation process.The blood coagulation Xa factor is effectively target site in anticoagulation therapy research.Zymoplasm is extracellular Insulin-Like serine protease, has vital role in coagulation process, and on the one hand, it can make the Fibrinogen cracking become scleroproein, and the latter participates in forming the hard clot suppository matrix; On the other hand, it can activate and assemble by induced platelet, and then causes the reaction of series of secondary coagulation cascade.
In human body, exist 3 kinds of anticoagulant substanceses to be regulated and controled coagulation process: the protein C of Antithrombin III, activation and tissue factor pathway inhibitor.Novel anticoagulant is usingd in blood coagulation waterfall the different factor as target, by acting on the factor such as Xa, thus the generation of blocking-up zymoplasm.In the end stage eventually of coagulation process, thrombin inhibitors can hinder fibrinous synthetic, and weakens the platelet activation process under thrombin induction.Xa factor is the thrombin that a kind of formation to zymoplasm has vital role.Xa factor participates in complicated Blood Coagulation Process, promotes that thrombogen is converted into zymoplasm, is to be responsible for the final enzyme that fibrin clot forms in coagulation cascade.Zymoplasm is split into fibrin monomer by Fibrinogen, and these monomers are in the generation of crosslinked rear promotion thrombotic disease.Suppress the formation that Xa factor can prevent zymoplasm, and then suppress to participate in thrombotic fibrinous formation.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of Pyrazolopyridine ketone compounds, it is desirable direct Xa factor inhibitor, it has the selectivity of height to Xa factor, also can suppress the Xa factor of bonding state except the Xa factor that can suppress to be unbound state, can be used for prevention or treatment thrombosis and other indications and comprise atrial fibrillation, acute coronary syndrome, acute symptomatic venous thrombosis and cerebral infarction, also can be used for Prevention or the treatment indication relevant to blood coagulation Xa factor function simultaneously.
For solving above technical problem, the present invention takes following technical scheme:
Compound with general formula (I), its pharmacologically acceptable salt, hydrate, prodrug or the meta-bolites that metabolism forms in any form,
Figure BDA0000134982560000021
Wherein: R 1for CN, CH 2cN, COOH, CH 2cOOH, COOC nh 2n+1, CH 2cOOC nh 2n+1, CONH 2, CH 2cONH 2, C (=NH) NH 2, CH 2c (=NH) NH 2, C (=NH) NHOH, CH 2c (=NH) NHOH, CHN 4, CH 2cHN 4, SO 2nH 2, CH 2sO 2nH 2, C 2hN 2o, CH 2c 2hN 2o, C 2n 2oC nh 2n+1and CH 2c 2n 2oC nh 2n+1;
R 2, R 3independently for replacing or unsubstituted phenyl ring or five yuan or hexa-member heterocycle;
R 4for OC nh 2n+1, OC mh 2mand OC ph 2p-1;
The integer that above-mentioned n is 1～6, the integer that m is 3～8, the integer that p is 3～6; Above-mentioned C nh 2n+1, C mh 2mand C ph 2p-1in hydrogen be not substituted, or partly or entirely be that fluorine replaces;
The described compound with general formula (I), in the meta-bolites of its pharmacologically acceptable salt, hydrate, prodrug and metabolism formation in any form, the hydrogen of commutativity is not substituted, or partly or entirely by deuterium, is replaced.
According to a preferred aspect of the present invention, in formula (I), R 1, R 3and R 4definition the same, R 2for
Figure BDA0000134982560000022
now, formula (I) compound is suc as formula shown in (II) or formula (III).
Figure BDA0000134982560000023
Further, R 3for replacing or unsubstituted hexa-member heterocycle, particularly preferably, R 3for
Figure BDA0000134982560000031
According to a further preferred aspect of the invention, in formula (I), R 3for replacing or unsubstituted hexa-member heterocycle, more preferably
Figure BDA0000134982560000032
r 1, R 2and R 4definition the same.
According to the present invention, formula (I) compound is specially a kind of in formula (VII) of the formula of being selected from (IV):
Figure BDA0000134982560000033
According to the present invention, described compound, it not only comprises certain single compound form, also comprise that various structures meets the form of mixtures of the compound of general formula (I) requirement, and such as racemic modification, enantiomer, diastereomer etc. of different isomerization bodily form formula of same compound.Described pharmacologically acceptable salt includes but not limited to hydrochloride, phosphoric acid salt, vitriol, acetate, maleate, mesylate, benzene sulfonate, benzoic acid salt, toluenesulfonate, succinate, fumarate, fumarate, tartrate, gallate, Citrate trianion etc.It is described that " prodrug with compound of general formula (I) " refers to a kind of material, after adopting appropriate means to use, can in subject, carry out metabolism or chemical reaction and be transformed at least one compound or its salt of structural formula (I).
Compound provided by the invention is the Pyrazolopyridine ketone compounds, it is desirable direct blood coagulation Xa factor inhibitor, it has the selectivity of height to Xa factor, also can suppress the Xa factor of bonding state except the Xa factor that can suppress to be unbound state, can be used for prevention or treatment thrombosis and other indications and comprise atrial fibrillation, acute coronary syndrome, acute symptomatic venous thrombosis and cerebral infarction, also can be used for Prevention or the treatment indication relevant to blood coagulation Xa factor function simultaneously.
Due to the enforcement of above technical scheme, the present invention compared with prior art has following advantage:
Compound first pass effect of the present invention is less, and effectively bioavailability is high, has using dosage during the indication relevant with blood coagulation Xa factor function in treatment few, the advantage that side effect is little.
Embodiment
Below in conjunction with specific embodiment, the present invention will be further described in detail, but the present invention is not limited to following examples.
Embodiment 1
The compound that the present embodiment provides a kind of formula (IV) to mean:
Embodiment 2
The compound that the present embodiment provides a kind of formula (V) to mean:
Figure BDA0000134982560000042
Embodiment 3
The compound that the present embodiment provides a kind of formula (IV) to mean:
Figure BDA0000134982560000051
Embodiment 4
The compound that the present embodiment provides a kind of formula (VII) to mean:
Above-described embodiment is only explanation technical conceive of the present invention and characteristics, and its purpose is to allow the person skilled in the art can understand content of the present invention and implement according to this, can not limit the scope of the invention with this.All equivalences that spirit is done according to the present invention change or modify, within all should being encompassed in protection scope of the present invention.

Claims (10)

1. the compound that there is general formula (I), its pharmacologically acceptable salt, hydrate, prodrug or the meta-bolites that metabolism forms in any form,
Figure FDA0000134982550000011
Wherein: R 1for CN, CH 2cN, COOH, CH 2cOOH, COOC nh 2n+1, CH 2cOOC nh 2n+1, CONH 2, CH 2cONH 2, C (=NH) NH 2, CH 2c (=NH) NH 2, C (=NH) NHOH, CH 2c (=NH) NHOH, CHN 4, CH 2cHN 4, SO 2nH 2, CH 2sO 2nH 2, C 2hN 2o, CH 2c 2hN 2o, C 2n 2oC nh 2n+1and CH 2c 2n 2oC nh 2n+1;
R 2, R 3independently for replacing or unsubstituted phenyl ring or five yuan or hexa-member heterocycle;
R 4for OC nh 2n+1, OC mh 2m andoC ph 2p-1;
The integer that above-mentioned n is 1～6, the integer that m is 3～8, the integer that p is 3～6;
Above-mentioned C nh 2n+1, C mh 2mand C ph 2p-1in hydrogen be not substituted, or partly or entirely be that fluorine replaces;
The described compound with general formula (I), in the meta-bolites of its pharmacologically acceptable salt, hydrate, prodrug and metabolism formation in any form, the hydrogen of commutativity is not substituted, or partly or entirely by deuterium, is replaced.
2. the compound with general formula (I) according to claim 1, its pharmacologically acceptable salt, hydrate, prodrug or the meta-bolites that metabolism forms in any form is characterized in that: in formula (I), R 2for
Figure FDA0000134982550000012
r 1, R 3and R 4definition with claim 1.
3. the compound with general formula (I) according to claim 2, its pharmacologically acceptable salt, hydrate, prodrug or the meta-bolites that metabolism forms in any form, is characterized in that: R 3for replacing or unsubstituted hexa-member heterocycle, R 1and R 4definition with claim 1.
4. the compound with general formula (I) according to claim 3, its pharmacologically acceptable salt, hydrate, prodrug or the meta-bolites that metabolism forms in any form, is characterized in that: R 3for
Figure FDA0000134982550000013
5. the compound with general formula (I) according to claim 1, its pharmacologically acceptable salt, hydrate, prodrug or the meta-bolites that metabolism forms in any form, is characterized in that: R 3for replacing or unsubstituted hexa-member heterocycle, R 1, R 2and R 4definition with claim 1.
6. the compound with general formula (I) according to claim 5, its pharmacologically acceptable salt, hydrate, prodrug or the meta-bolites that metabolism forms in any form, is characterized in that: R 3for
Figure FDA0000134982550000021
7. the compound with general formula (I) according to claim 1, its pharmacologically acceptable salt, hydrate, prodrug or the meta-bolites that metabolism forms in any form is characterized in that: described compound is for being selected from a kind of in formula (VII) of formula (IV):
Figure FDA0000134982550000022
8. the described compound with general formula (I) of any one claim in claim 1 to 7, its pharmacologically acceptable salt, hydrate, prodrug or metabolism forms in any form meta-bolites prevent and/or treat the purposes in the medicine of the indication relevant to direct factor Xa function in preparation.
9. purposes according to claim 8, it is characterized in that: the described indication relevant to blood coagulation Xa factor function comprises thrombosis, atrial fibrillation, acute coronary syndrome, acute symptomatic venous thrombosis and cerebral infarction.
10. one kind includes the described compound with general formula (I) of any one claim in claim 1 to 7, its pharmacologically acceptable salt, hydrate, the anticoagulant pharmaceutical composition of prodrug or the meta-bolites that metabolism forms in any form.
CN2012100297451A 2012-02-10 2012-02-10 Pyrazolo pyridone compound and its application in preparation of anticoagulant Pending CN103242310A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN2012100297451A CN103242310A (en) 2012-02-10 2012-02-10 Pyrazolo pyridone compound and its application in preparation of anticoagulant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN2012100297451A CN103242310A (en) 2012-02-10 2012-02-10 Pyrazolo pyridone compound and its application in preparation of anticoagulant

Publications (1)

Publication Number Publication Date
CN103242310A true CN103242310A (en) 2013-08-14

Family

ID=48922215

Family Applications (1)

Application Number Title Priority Date Filing Date
CN2012100297451A Pending CN103242310A (en) 2012-02-10 2012-02-10 Pyrazolo pyridone compound and its application in preparation of anticoagulant

Country Status (1)

Country Link
CN (1) CN103242310A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014044113A1 (en) * 2012-09-18 2014-03-27 上海恒瑞医药有限公司 Pyrazol[3,4-c] pyridine derivative, preparation method and use in medicine thereof
CN104311558A (en) * 2014-09-19 2015-01-28 广东东阳光药业有限公司 Pyrazolo piperidone compound containing cyclohexane substituent and composition and application thereof
CN104513239A (en) * 2014-12-10 2015-04-15 沈阳药科大学 Pyrazolo[3, 4-c]pyridine-7-one compound and application thereof
CN104557930A (en) * 2015-02-14 2015-04-29 佛山市赛维斯医药科技有限公司 Blood coagulation factor Xa inhibitor containing bicycle-amide structure and application thereof
CN104557928A (en) * 2015-02-14 2015-04-29 佛山市赛维斯医药科技有限公司 Blood coagulation factor Xa inhibitor containing bicycle-amide structure, as well as preparation and application thereof
CN104557929A (en) * 2015-02-14 2015-04-29 佛山市赛维斯医药科技有限公司 Blood coagulation factor Xa inhibitor containing bicycle-amide structure and application thereof
CN104592227A (en) * 2015-02-14 2015-05-06 佛山市赛维斯医药科技有限公司 Amide and halogeno benzene structure-contained FXalpha inhibitor, as well as preparation method and application of thereof
CN104672234A (en) * 2015-02-14 2015-06-03 佛山市赛维斯医药科技有限公司 FXa inhibitors containing bisamide structure as well as preparation method and application thereof
CN105085515A (en) * 2014-05-22 2015-11-25 南京明德新药研发股份有限公司 Hydrazide compound as blood coagulation factor Xa inhibitor
WO2015176625A1 (en) * 2014-05-22 2015-11-26 南京明德新药研发股份有限公司 HYDRAZINE COMPOUND AS BLOOD COAGULATION FACTOR Xa INHIBITOR
JP2016537424A (en) * 2013-11-18 2016-12-01 チュヨンドゥ イーストン バイオファーマシューティカルズ カンパニー リミテッドＣｈｅｎｇｄｕ Ｅａｓｔｏｎ Ｂｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｃｏ．， Ｌｔｄ． Pyridine derivatives and their medical use

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1439008A (en) * 2000-06-23 2003-08-27 布里斯托尔-迈尔斯斯奎布药品公司 1-(heteroaryl-henyl)-condensed pyrazol derivatives as factor XA inhibitors
US20030181466A1 (en) * 2001-12-10 2003-09-25 Jiacheng Zhou Synthesis of 4,5-dihydro-pyrazolo [3,4-c] pyrid-2-ones
US20040220174A1 (en) * 2001-09-21 2004-11-04 Pinto Donald J.P. Lactam-containing compounds and derivatives thereof as factor Xa inhibitors
CN1578660A (en) * 2001-09-21 2005-02-09 百时美施贵宝公司 Lactam-containing compounds and derivatives thereof as factor xa inhibitors
US20090030045A1 (en) * 2006-05-05 2009-01-29 Millennium Pharmaceuticals, Inc. Factor xa inhibitors

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1439008A (en) * 2000-06-23 2003-08-27 布里斯托尔-迈尔斯斯奎布药品公司 1-(heteroaryl-henyl)-condensed pyrazol derivatives as factor XA inhibitors
US20040220174A1 (en) * 2001-09-21 2004-11-04 Pinto Donald J.P. Lactam-containing compounds and derivatives thereof as factor Xa inhibitors
CN1578660A (en) * 2001-09-21 2005-02-09 百时美施贵宝公司 Lactam-containing compounds and derivatives thereof as factor xa inhibitors
US20030181466A1 (en) * 2001-12-10 2003-09-25 Jiacheng Zhou Synthesis of 4,5-dihydro-pyrazolo [3,4-c] pyrid-2-ones
US20090030045A1 (en) * 2006-05-05 2009-01-29 Millennium Pharmaceuticals, Inc. Factor xa inhibitors

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104039788B (en) * 2012-09-18 2015-10-14 上海恒瑞医药有限公司 Pyrazolo [3,4-c] pyridine derivatives, its preparation method and in application pharmaceutically
CN104039788A (en) * 2012-09-18 2014-09-10 上海恒瑞医药有限公司 Pyrazol[3,4-c] pyridine derivative, preparation method and use in medicine thereof
WO2014044113A1 (en) * 2012-09-18 2014-03-27 上海恒瑞医药有限公司 Pyrazol[3,4-c] pyridine derivative, preparation method and use in medicine thereof
JP2016537424A (en) * 2013-11-18 2016-12-01 チュヨンドゥ イーストン バイオファーマシューティカルズ カンパニー リミテッドＣｈｅｎｇｄｕ Ｅａｓｔｏｎ Ｂｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｃｏ．， Ｌｔｄ． Pyridine derivatives and their medical use
CN105085515A (en) * 2014-05-22 2015-11-25 南京明德新药研发股份有限公司 Hydrazide compound as blood coagulation factor Xa inhibitor
CN105085515B (en) * 2014-05-22 2019-02-01 华北制药股份有限公司 Hydrazide kind compound as coagulation factor xa inhibitors
US9938272B2 (en) 2014-05-22 2018-04-10 North China Pharmaceutical Company., Ltd. Hydrazine compound as blood coagulation factor Xa inhibitor
JP2017516845A (en) * 2014-05-22 2017-06-22 ノース チャイナ ファーマシューティカル カンパニー リミテッド Hydrazide compounds as blood coagulation factor Xa inhibitors
WO2015176625A1 (en) * 2014-05-22 2015-11-26 南京明德新药研发股份有限公司 HYDRAZINE COMPOUND AS BLOOD COAGULATION FACTOR Xa INHIBITOR
CN104311558B (en) * 2014-09-19 2016-06-01 广东东阳光药业有限公司 Pyrazoles containing hexanaphthene substituting group piperidone compounds and composition thereof and purposes
CN104311558A (en) * 2014-09-19 2015-01-28 广东东阳光药业有限公司 Pyrazolo piperidone compound containing cyclohexane substituent and composition and application thereof
CN104513239B (en) * 2014-12-10 2017-08-22 沈阳药科大学 The ketone compounds of pyrazolo [3,4 c] pyridine 7 and its application
CN104513239A (en) * 2014-12-10 2015-04-15 沈阳药科大学 Pyrazolo[3, 4-c]pyridine-7-one compound and application thereof
CN104672234A (en) * 2015-02-14 2015-06-03 佛山市赛维斯医药科技有限公司 FXa inhibitors containing bisamide structure as well as preparation method and application thereof
CN104557928B (en) * 2015-02-14 2016-08-24 佛山市赛维斯医药科技有限公司 A kind of containing bicyclic amide structure coagulation factor xa inhibitors, Its Preparation Method And Use
CN104557929B (en) * 2015-02-14 2016-06-01 佛山市赛维斯医药科技有限公司 One class contains coagulation factor xa inhibitors and the purposes thereof of bicyclic amide structure
CN104557930A (en) * 2015-02-14 2015-04-29 佛山市赛维斯医药科技有限公司 Blood coagulation factor Xa inhibitor containing bicycle-amide structure and application thereof
CN104557928A (en) * 2015-02-14 2015-04-29 佛山市赛维斯医药科技有限公司 Blood coagulation factor Xa inhibitor containing bicycle-amide structure, as well as preparation and application thereof
CN104592227A (en) * 2015-02-14 2015-05-06 佛山市赛维斯医药科技有限公司 Amide and halogeno benzene structure-contained FXalpha inhibitor, as well as preparation method and application of thereof
CN104557929A (en) * 2015-02-14 2015-04-29 佛山市赛维斯医药科技有限公司 Blood coagulation factor Xa inhibitor containing bicycle-amide structure and application thereof

Similar Documents

Publication Publication Date Title
CN103242310A (en) Pyrazolo pyridone compound and its application in preparation of anticoagulant
CN101743001A (en) With the combination of compounds anticoagulant therapy that plays the factor XA inhibitor effect
US9126979B2 (en) Compounds for inhibiting the interaction of BCL2 with binding partners
MX2014007731A (en) Compounds for inhibiting the interaction of bcl2 with binding partners.
ATE284860T1 (en) NEW USE OF PHENYLHETEROALKYLAMINE DERIVATIVES
TW201216963A (en) Novel compounds and compositions for the inhibition of NAMPT
NO20051265L (en) Use of and some new imidazopyridines
CA3234641A1 (en) Compounds and compositions for the treatment or prevention of pathological conditions associated with excess fibrin deposition and/or thrombus formation
MX2014007732A (en) Compounds for inhibiting the interaction of bcl2 with binding partners.
MX2011012559A (en) Lxr modulators.
TW200745136A (en) 4-Amino-thieno[3,2-c]pyridine-7-carboxylic acid derivatives
MXPA03010341A (en) Use of compounds with combined nep/mp-inhibitory activity in the preparation of medicaments.
DE60305514D1 (en) NEW USE OF BENZOTHIAZONE DERIVATIVES
NZ592615A (en) Method for treating or preventing thrombosis using 150 mg b.i.d. of dabigatran etexilate or a salt thereof with improved efficacy over conventional warfarin therapy
MX2014007729A (en) Compounds for inhibiting the interaction of bcl2 with binding partners.
MX2014007725A (en) Compounds for inhibiting the interaction of bcl2 with binding partners.
JP3963301B2 (en) Pharmaceutical composition containing a tetrahydroisoquinoline compound
NZ592613A (en) Method for treating or preventing thrombosis using >150 mg to 300 mg b.i.d. of dabigatran etexilate or a salt thereof with improved efficacy over conventional warfarin therapy
ZA200506328B (en) 2-(butyl-1sylfonylamino)-N-Ä1(R)-6methoxy-pyridin-3-yl)-propylÜ-benzamid, the use thereof in the form of drug an pharmaceutical preperations containing said compound
CN102167689A (en) Preparation method of chiral warfarin and chiral warfarin derivatives
TW201006469A (en) Use of HDAC inhibitors for the treatment of acute myeloid leukemia and/or myelodysplastic syndrome
CN104098647A (en) Argatroban analogue and preparation method and medical application thereof
CN102649787A (en) (benzimidazole-2-yl)pyridine derivative and application thereof to preparation of anticoagulant medicines
DE60103035D1 (en) NEW USE OF PHENYLHETEROALKYLAMINE DERIVATIVES
CN103570684A (en) Phenylamine benzimidazole derivative and application of phenylamine benzimidazole derivative in preparation of anticoagulation medicine

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C05 Deemed withdrawal (patent law before 1993)
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20130814