WO2016206576A1 - 一种氘代噻吩并哌啶衍生物、制备方法及其应用 - Google Patents
一种氘代噻吩并哌啶衍生物、制备方法及其应用 Download PDFInfo
- Publication number
- WO2016206576A1 WO2016206576A1 PCT/CN2016/086538 CN2016086538W WO2016206576A1 WO 2016206576 A1 WO2016206576 A1 WO 2016206576A1 CN 2016086538 W CN2016086538 W CN 2016086538W WO 2016206576 A1 WO2016206576 A1 WO 2016206576A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- pharmaceutically acceptable
- acceptable salt
- phenyl
- hydrogen
- Prior art date
Links
- 0 *OC([C@@](c1ccccc1Cl)O)=O Chemical compound *OC([C@@](c1ccccc1Cl)O)=O 0.000 description 1
- GKTWGGQPFAXNFI-HNNXBMFYSA-N COC([C@H](c1ccccc1Cl)N(CC1)Cc2c1[s]cc2)=O Chemical compound COC([C@H](c1ccccc1Cl)N(CC1)Cc2c1[s]cc2)=O GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 1
- RWOLDZZTBNYTMS-SSDOTTSWSA-N O[C@@H](C(O)=O)c1ccccc1Cl Chemical compound O[C@@H](C(O)=O)c1ccccc1Cl RWOLDZZTBNYTMS-SSDOTTSWSA-N 0.000 description 1
Images
Classifications
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4535—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom, e.g. pizotifen
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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 System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Entry | Compound | Dose(mg/kg) | TailBleedingTime(s) |
1 | Vehicle | — | 158 |
2 | TSC-6 | 1.0 | 635 |
3 | I-1 | 1.0 | 950 |
4 | TSD-6 | 1.0 | 1331* |
5 | Clopidogrel | 10 | 1896*** |
Entry | Compound | Dose(mg/kg) | Thrombus(mg) |
1 | Vehicle | — | 52.2 |
2 | TSC-6 | 1.0 | 31.4* |
3 | I-1 | 1.0 | 25.6 |
4 | TSD-6 | 1.0 | 18.4* |
5 | Clopidogrel | 10 | 20.1** |
Claims (10)
- 权利要求1所述氘代噻吩并哌啶衍生物或其可药用盐,其特征在于,其中,X为P,m为0,n为0,R1选自氢、CH3-、CH3CH2-、异丙基、CCl3CH2-,苯基;R2选自氢、CH3-、CH3CH2-、异丙基、CCl3CH2-,苯基。
- 权利要求1所述氘代噻吩并哌啶衍生物或其可药用盐,其特征在于,其中,X为P,m为1,n为1,R1选自氢、CH3-、CH3CH2-、异丙基、CCL3CH2-,叔丁基,苯基;R2选自氢、CH3-、CH3CH2-、异丙基、CCl3CH2-,叔丁基,苯基。
- 权利要求1所述氘代噻吩并哌啶衍生物或其可药用盐,其特征在于,其中,X为S,m为0,n为0,R1选自氢、CH3-、CH3CH2-、异丙基、CCl3CH2-,叔丁基,苯基;R2为无取代,且X与O形成双键。
- 权利要求1所述氘代噻吩并哌啶磷酸酯衍生物或其可药用盐,其中,所述盐可以是氘代噻吩并哌啶磷酸酯衍生物与硫酸、盐酸、氢溴酸、磷酸、酒石酸、富马酸、马来酸、柠檬酸、乙酸、甲酸、甲磺酸、对甲苯磺酸、草酸或琥珀酸形成的盐。
- 一种药物组合物,其特征在于,所述药物组合物含有权利要求1所述的氘代噻吩并哌啶磷酸酯衍生物或其可药用盐。
- 权利要求7所述的药物组合物,其特征在于,所述药物组合物还含有药学上可接受的载体。
- 权利要求1所述的氘代噻吩并哌啶磷酸酯衍生物或其可药用盐在制备治疗和预防心力 衰竭、中风、不稳定心绞痛等心脑血管疾病药物中的应用。
- 权利要求1所述的氘代噻吩并哌啶磷酸酯衍生物或其可药用盐,在制备抗血小板凝集的药物中的应用。
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2016282124A AU2016282124B2 (en) | 2015-06-23 | 2016-06-21 | Deuterated thienopiperidine derivatives, manufacturing method, and application thereof |
JP2017564689A JP6695361B2 (ja) | 2015-06-23 | 2016-06-21 | 重水素化チエノピペリジン誘導体、調製方法、及びその使用 |
EP16813692.7A EP3315505B1 (en) | 2015-06-23 | 2016-06-21 | Deuterated thienopiperidine derivatives, manufacturing method, and application thereof |
US15/739,337 US11130766B2 (en) | 2015-06-23 | 2016-06-21 | Deuterated thienopiperidine derivatives, manufacturing method, and application thereof |
CN201680036795.9A CN107922448B (zh) | 2015-06-23 | 2016-06-21 | 一种氘代噻吩并哌啶衍生物、制备方法及其应用 |
KR1020187001571A KR20180020223A (ko) | 2015-06-23 | 2016-06-21 | 중수소화된 티에노피페리딘 유도체, 제조방법 및 그 응용 |
CA2990734A CA2990734A1 (en) | 2015-06-23 | 2016-06-21 | Deuterated thienopiperidine derivatives, manufacturing method and application thereof |
RU2018100116A RU2716141C2 (ru) | 2015-06-23 | 2016-06-21 | Дейтерированные производные тиенопиперидина, способ их получения и применение |
ZA2018/00493A ZA201800493B (en) | 2015-06-23 | 2018-01-23 | Deuterated thienopiperidine derivatives, manufacturing method, and application thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510352739.3 | 2015-06-23 | ||
CN201510352739 | 2015-06-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2016206576A1 true WO2016206576A1 (zh) | 2016-12-29 |
Family
ID=57584702
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2016/086538 WO2016206576A1 (zh) | 2015-06-23 | 2016-06-21 | 一种氘代噻吩并哌啶衍生物、制备方法及其应用 |
Country Status (10)
Country | Link |
---|---|
US (1) | US11130766B2 (zh) |
EP (1) | EP3315505B1 (zh) |
JP (1) | JP6695361B2 (zh) |
KR (1) | KR20180020223A (zh) |
CN (2) | CN107698620A (zh) |
AU (1) | AU2016282124B2 (zh) |
CA (1) | CA2990734A1 (zh) |
RU (1) | RU2716141C2 (zh) |
WO (1) | WO2016206576A1 (zh) |
ZA (1) | ZA201800493B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105983016B (zh) | 2015-03-23 | 2023-08-11 | 天士力医药集团股份有限公司 | 一种含有水飞蓟宾的药物组合 |
CN107698620A (zh) | 2015-06-23 | 2018-02-16 | 江苏天士力帝益药业有限公司 | 一种氘代噻吩并哌啶衍生物、制备方法及其应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103665042A (zh) * | 2012-09-21 | 2014-03-26 | 北京普禄德医药科技有限公司 | 光学活性的2-羟基四氢噻吩并吡啶衍生物及其制备方法和用途 |
WO2014043895A1 (zh) * | 2012-09-21 | 2014-03-27 | 北京普禄德医药科技有限公司 | 光学活性的2-羟基四氢噻吩并吡啶衍生物及其制备方法和用途 |
CN104418891A (zh) * | 2013-08-28 | 2015-03-18 | 江苏威凯尔医药科技有限公司 | 水溶性2-羟基四氢噻吩并吡啶衍生物的制备及其医药用途 |
CN104447867A (zh) * | 2013-09-17 | 2015-03-25 | 天士力控股集团有限公司 | 一种噻吩并哌啶衍生物、制备方法及其应用 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2530247B1 (fr) | 1982-07-13 | 1986-05-16 | Sanofi Sa | Nouveaux derives de la thieno (3, 2-c) pyridine, leur procede de preparation et leur application therapeutique |
FR2576901B1 (fr) | 1985-01-31 | 1987-03-20 | Sanofi Sa | Nouveaux derives de l'acide a-(oxo-2 hexahydro-2,4,5,6,7,7a thieno (3,2-c) pyridyl-5) phenyl acetique, leur procede de preparation et leur application therapeutique |
FR2623810B2 (fr) | 1987-02-17 | 1992-01-24 | Sanofi Sa | Sels de l'alpha-(tetrahydro-4,5,6,7 thieno(3,2-c) pyridyl-5) (chloro-2 phenyl) -acetate de methyle dextrogyre et compositions pharmaceutiques en contenant |
FR2652579B1 (fr) | 1989-10-02 | 1992-01-24 | Sanofi Sa | Derives d'hydroxy-2 thiophene et furanne condenses avec un cycle azote, sur procede de preparation et leur application en therapeutique. |
US6221335B1 (en) * | 1994-03-25 | 2001-04-24 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
FR2744918B1 (fr) | 1996-02-19 | 1998-05-07 | Sanofi Sa | Nouvelles associations de principes actifs contenant un derive de thieno(3,2-c)pyridine et un antithrombotique |
JPH10310586A (ja) | 1996-06-26 | 1998-11-24 | Sankyo Co Ltd | ヒドロピリジン類の新規医薬用途 |
WO1997049397A1 (fr) | 1996-06-26 | 1997-12-31 | Sankyo Company, Limited | Nouvelles compositions medicinales d'hydropyridines |
FR2779726B1 (fr) | 1998-06-15 | 2001-05-18 | Sanofi Sa | Forme polymorphe de l'hydrogenosulfate de clopidogrel |
US6440710B1 (en) * | 1998-12-10 | 2002-08-27 | The Scripps Research Institute | Antibody-catalyzed deuteration, tritiation, dedeuteration or detritiation of carbonyl compounds |
PT1104760E (pt) * | 1999-12-03 | 2003-06-30 | Pfizer Prod Inc | Compostos de sulfamoil-heteroarilpirazole como agentes analgesicos e anti-inflamatorios |
TW200413273A (en) * | 2002-11-15 | 2004-08-01 | Wako Pure Chem Ind Ltd | Heavy hydrogenation method of heterocyclic rings |
CA2624179A1 (en) * | 2005-10-06 | 2007-04-12 | Auspex Pharmaceuticals, Inc. | Deuterated inhibitors of gastric h+, k+-atpase with enhanced therapeutic properties |
US7750168B2 (en) * | 2006-02-10 | 2010-07-06 | Sigma-Aldrich Co. | Stabilized deuteroborane-tetrahydrofuran complex |
TWI392681B (zh) | 2006-04-06 | 2013-04-11 | Daiichi Sankyo Co Ltd | 高純度普拉格雷及其酸加成鹽之製法 |
US20080319004A1 (en) * | 2007-06-19 | 2008-12-25 | Protia, Llc | Deuterium-enriched clopidogrel |
CN101591344B (zh) | 2008-05-27 | 2012-12-05 | 连云港恒邦医药科技有限公司 | 一种抗血栓的化合物、其制备方法和用途 |
TWI523652B (zh) | 2008-07-15 | 2016-03-01 | 泰瑞克公司 | 氘化苄基苯衍生物及使用方法 |
CN101885730B (zh) | 2009-05-13 | 2012-07-04 | 连云港恒邦医药科技有限公司 | 抗血栓的化合物 |
WO2011079407A1 (zh) | 2009-12-28 | 2011-07-07 | 北京益君康医药技术有限公司 | 新的具有抗凝血作用的化合物 |
CN102120744B (zh) | 2010-02-02 | 2013-01-09 | 江苏威凯尔医药科技有限公司 | 光学活性2-羟基四氢噻吩并吡啶衍生物及其制备方法与在制药中的用途 |
US20120329762A1 (en) | 2011-06-27 | 2012-12-27 | Ashok Kumar | Anti-thrombotic compounds |
CN103554132B (zh) * | 2013-10-31 | 2016-01-27 | 李纪宁 | 四氢噻吩并吡啶氘代衍生物及其制备方法和药物用途 |
CN107698620A (zh) * | 2015-06-23 | 2018-02-16 | 江苏天士力帝益药业有限公司 | 一种氘代噻吩并哌啶衍生物、制备方法及其应用 |
-
2016
- 2016-06-20 CN CN201610446961.4A patent/CN107698620A/zh active Pending
- 2016-06-21 AU AU2016282124A patent/AU2016282124B2/en not_active Ceased
- 2016-06-21 US US15/739,337 patent/US11130766B2/en active Active
- 2016-06-21 CN CN201680036795.9A patent/CN107922448B/zh active Active
- 2016-06-21 EP EP16813692.7A patent/EP3315505B1/en active Active
- 2016-06-21 JP JP2017564689A patent/JP6695361B2/ja not_active Expired - Fee Related
- 2016-06-21 KR KR1020187001571A patent/KR20180020223A/ko not_active Application Discontinuation
- 2016-06-21 WO PCT/CN2016/086538 patent/WO2016206576A1/zh active Application Filing
- 2016-06-21 CA CA2990734A patent/CA2990734A1/en active Pending
- 2016-06-21 RU RU2018100116A patent/RU2716141C2/ru active
-
2018
- 2018-01-23 ZA ZA2018/00493A patent/ZA201800493B/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103665042A (zh) * | 2012-09-21 | 2014-03-26 | 北京普禄德医药科技有限公司 | 光学活性的2-羟基四氢噻吩并吡啶衍生物及其制备方法和用途 |
WO2014043895A1 (zh) * | 2012-09-21 | 2014-03-27 | 北京普禄德医药科技有限公司 | 光学活性的2-羟基四氢噻吩并吡啶衍生物及其制备方法和用途 |
CN104418891A (zh) * | 2013-08-28 | 2015-03-18 | 江苏威凯尔医药科技有限公司 | 水溶性2-羟基四氢噻吩并吡啶衍生物的制备及其医药用途 |
CN104447867A (zh) * | 2013-09-17 | 2015-03-25 | 天士力控股集团有限公司 | 一种噻吩并哌啶衍生物、制备方法及其应用 |
Also Published As
Publication number | Publication date |
---|---|
EP3315505A4 (en) | 2019-02-27 |
RU2018100116A3 (zh) | 2019-09-30 |
JP2018520128A (ja) | 2018-07-26 |
EP3315505B1 (en) | 2020-03-25 |
JP6695361B2 (ja) | 2020-05-20 |
AU2016282124B2 (en) | 2020-11-05 |
CA2990734A1 (en) | 2016-12-29 |
KR20180020223A (ko) | 2018-02-27 |
EP3315505A1 (en) | 2018-05-02 |
RU2716141C2 (ru) | 2020-03-06 |
CN107922448A (zh) | 2018-04-17 |
CN107698620A (zh) | 2018-02-16 |
CN107922448B (zh) | 2020-06-12 |
ZA201800493B (en) | 2020-05-27 |
RU2018100116A (ru) | 2019-07-23 |
AU2016282124A1 (en) | 2018-01-18 |
US11130766B2 (en) | 2021-09-28 |
US20180179222A1 (en) | 2018-06-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI290927B (en) | 2-Acetoxy-5-(alpha-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine acid-additive salts | |
JP4316794B2 (ja) | イソキノリン誘導体及び医薬 | |
JP6622205B2 (ja) | チエノピペリジン誘導体およびその使用 | |
JP2019135258A (ja) | 第Xa因子阻害剤の結晶形態 | |
JP5575979B2 (ja) | シアノ基を含有するチエノピリジンエステル誘導体、その調製方法、使用および組成物 | |
US20040235877A1 (en) | Novel use of tricyclic compound | |
BR112012007828B1 (pt) | compostos inibidores da xantina oxidase, processo para preparar os compostos, e, composição farmacêutica para a inibição da xantina oxidase | |
CA3111725A1 (en) | 2,6-diamino pyridine compounds | |
JPH0428269B2 (zh) | ||
CN105384739A (zh) | 吡唑并[3,4-c]吡啶类衍生物 | |
WO2016206576A1 (zh) | 一种氘代噻吩并哌啶衍生物、制备方法及其应用 | |
JP2005527518A (ja) | 新規なカルコン(chalcone)誘導体とその使用 | |
JP5796872B2 (ja) | 第Xa因子阻害剤の結晶性塩 | |
JP2020533401A (ja) | 不飽和脂肪族オレフィン性結合を含有するチエノピリジン誘導体、その調製方法および使用 | |
JPS63222170A (ja) | エルゴリニルヘテロサイクル類 | |
JP2756941B2 (ja) | 2−クロロ−3−アリールアミノ−1,4−ナフトキノン誘導体の血小板凝集抑制剤としての用途 | |
JPH04120072A (ja) | アンジオテンシン2拮抗性ピリミジン誘導体 | |
JP3000288B2 (ja) | 新規なジアゾシン誘導体 | |
JP3571114B2 (ja) | 麻薬拮抗剤 | |
JP2955768B2 (ja) | 新規なジアゾシン誘導体 | |
JP2001114699A (ja) | キマーゼ阻害作用を有する化合物を有効成分とする血管新生阻害剤 | |
CS228943B2 (cs) | Způsob výroby substituovaných derivátů 1,4-dihydropyridinu | |
JP2001181186A (ja) | ピリド[4,3−b][1,6]ナフチリジン誘導体を有効成分として含有する肝疾患治療剤 | |
CZ215992A3 (cs) | Nové acylaminohetrazepinové deriváty, způsob výroby a farmaceutické prostředky sjejích obsahem | |
JPH09512836A (ja) | 細胞付着抑制剤としての(−)−(3r)−3−メチル−4−{4−[4−(4−ピリジル)ピペラジン−1−イル]フェノキシ}酪酸 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 16813692 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2017564689 Country of ref document: JP Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 2990734 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 15739337 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 20187001571 Country of ref document: KR Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 2016282124 Country of ref document: AU Date of ref document: 20160621 Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2018100116 Country of ref document: RU Ref document number: 2016813692 Country of ref document: EP |