CN100582112C - 用作PDE7抑制剂的4-氨基噻吩并[2,3-d]嘧啶-6-甲腈衍生物 - Google Patents

用作PDE7抑制剂的4-氨基噻吩并[2,3-d]嘧啶-6-甲腈衍生物 Download PDF

Info

Publication number
CN100582112C
CN100582112C CN200480007362A CN200480007362A CN100582112C CN 100582112 C CN100582112 C CN 100582112C CN 200480007362 A CN200480007362 A CN 200480007362A CN 200480007362 A CN200480007362 A CN 200480007362A CN 100582112 C CN100582112 C CN 100582112C
Authority
CN
China
Prior art keywords
methyl
pyrimidine
carbonitrile
thieno
amino
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.)
Expired - Fee Related
Application number
CN200480007362A
Other languages
English (en)
Chinese (zh)
Other versions
CN1761671A (zh
Inventor
E·特里卡布拉斯贝拉特
V·M·塞加拉马塔莫罗斯
J·阿尔瓦雷斯-布伊拉戈麦斯
J·J·瓦凯罗洛佩斯
J·M·明格斯奥尔特加
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.)
Almirall SA
Original Assignee
Almirall Prodesfarma SA
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 Almirall Prodesfarma SA filed Critical Almirall Prodesfarma SA
Publication of CN1761671A publication Critical patent/CN1761671A/zh
Application granted granted Critical
Publication of CN100582112C publication Critical patent/CN100582112C/zh
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Epidemiology (AREA)
  • Transplantation (AREA)
  • Pain & Pain Management (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Neurosurgery (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CN200480007362A 2003-01-23 2004-01-23 用作PDE7抑制剂的4-氨基噻吩并[2,3-d]嘧啶-6-甲腈衍生物 Expired - Fee Related CN100582112C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ES200300172A ES2217956B1 (es) 2003-01-23 2003-01-23 Nuevos derivados de 4-aminotieno(2,3-d)pirimidin-6-carbonitrilo.
ESP200300172 2003-01-23

Publications (2)

Publication Number Publication Date
CN1761671A CN1761671A (zh) 2006-04-19
CN100582112C true CN100582112C (zh) 2010-01-20

Family

ID=32749101

Family Applications (1)

Application Number Title Priority Date Filing Date
CN200480007362A Expired - Fee Related CN100582112C (zh) 2003-01-23 2004-01-23 用作PDE7抑制剂的4-氨基噻吩并[2,3-d]嘧啶-6-甲腈衍生物

Country Status (8)

Country Link
US (1) US7662814B2 (enExample)
EP (1) EP1590352B1 (enExample)
JP (1) JP2006515604A (enExample)
CN (1) CN100582112C (enExample)
AT (1) ATE365742T1 (enExample)
DE (1) DE602004007239T2 (enExample)
ES (2) ES2217956B1 (enExample)
WO (1) WO2004065391A1 (enExample)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7763627B2 (en) * 2003-04-09 2010-07-27 Exelixis, Inc. Tie-2 modulators and methods of use
US20060014165A1 (en) * 2003-07-14 2006-01-19 Decode Genetics Ehf. Methods of diagnosis and treatment for asthma and other respiratory diseases based on haplotype association
EP1806347A4 (en) * 2004-10-08 2009-07-01 Astellas Pharma Inc PYRIMIDINE DERIVATIVES FUSED WITH AN AROMATIC RING
TW200621257A (en) * 2004-10-20 2006-07-01 Astellas Pharma Inc Pyrimidine derivative fused with nonaromatic ring
GB0423653D0 (en) 2004-10-25 2004-11-24 Piramed Ltd Pharmaceutical compounds
WO2007117995A2 (en) * 2006-03-30 2007-10-18 Takeda San Diego, Inc. Kinase inhibitors
EP2041139B1 (en) 2006-04-26 2011-11-09 F. Hoffmann-La Roche AG Pharmaceutical compounds
KR101402474B1 (ko) * 2006-04-26 2014-06-19 제넨테크, 인크. 포스포이노시티드 3-키나제 억제제 화합물 및 이를 포함하는 약학적 조성물
BRPI0710874A2 (pt) 2006-04-26 2012-02-14 Hoffmann La Roche compostos de tienopirimidina, processos de produção dos referidos compostos, composições farmacêuticas contendo os mesmos, kit, produto, e usos dos compostos
GB0608820D0 (en) * 2006-05-04 2006-06-14 Piramed Ltd Pharmaceutical compounds
JP2009539988A (ja) 2006-06-12 2009-11-19 バーテックス ファーマシューティカルズ インコーポレイテッド イオンチャネルの調節因子として有用なチエノピリミジン
KR101507182B1 (ko) * 2006-12-07 2015-03-30 제넨테크, 인크. 포스포이노시타이드 3-키나제 억제제 화합물 및 그의 사용 방법
TWI499420B (zh) 2006-12-07 2015-09-11 Hoffmann La Roche 肌醇磷脂３-激酶抑制劑化合物及使用方法
US8637528B2 (en) * 2007-03-27 2014-01-28 Omeros Corporation Use of PDE7 inhibitors for the treatment of movement disorders
CN101917992A (zh) 2007-03-27 2010-12-15 奥默罗斯公司 用于治疗运动障碍的pde7抑制剂的用途
CA2699202C (en) * 2007-09-12 2016-09-27 F. Hoffmann-La Roche Ag Combinations of phosphoinositide 3-kinase inhibitor compounds and chemotherapeutic agents, and methods of use
CA2704711C (en) * 2007-09-24 2016-07-05 Genentech, Inc. Thiazolopyrimidine p13k inhibitor compounds and methods of use
US8354528B2 (en) 2007-10-25 2013-01-15 Genentech, Inc. Process for making thienopyrimidine compounds
GB0721095D0 (en) 2007-10-26 2007-12-05 Piramed Ltd Pharmaceutical compounds
US20100093714A1 (en) * 2008-10-13 2010-04-15 Devraj Chakravarty AMIDES OF THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS
US20100093702A1 (en) * 2008-10-13 2010-04-15 Barbay J Kent METHYLENE AMINES OF THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS
WO2010103130A2 (en) * 2009-03-13 2010-09-16 Katholieke Universiteit Leuven, K.U.Leuven R&D Novel bicyclic heterocycles
SG182247A1 (en) * 2009-05-27 2012-08-30 Hoffmann La Roche Bicyclic indole-pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use
SG175708A1 (en) * 2009-05-27 2011-12-29 Genentech Inc Bicyclic pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use
JP6042331B2 (ja) 2010-07-23 2016-12-14 プレジデント アンド フェローズ オブ ハーバード カレッジ プロテアソーム活性を向上させる三環系化合物
EP4275752A3 (en) * 2010-11-08 2024-02-21 Omeros Corporation Treatment of addiction and impulse-control disorders using pde7 inhibitors
US9220715B2 (en) 2010-11-08 2015-12-29 Omeros Corporation Treatment of addiction and impulse-control disorders using PDE7 inhibitors
AR090037A1 (es) * 2011-11-15 2014-10-15 Xention Ltd Derivados de tieno y/o furo-pirimidinas y piridinas inhibidores de los canales de potasio
WO2013078126A1 (en) 2011-11-23 2013-05-30 Cancer Research Technology Limited Thienopyrimidine inhibitors of atypical protein kinase c
AU2013202373B2 (en) * 2012-01-25 2016-04-14 Proteostasis Therapeutics, Inc. Proteasome activity enhancing compounds
EP2806875B1 (en) * 2012-01-25 2017-07-19 Proteostasis Therapeutics, Inc. Proteasome activity modulating compounds
CN113372358B (zh) 2012-09-28 2024-05-14 武田药品工业株式会社 噻吩并嘧啶衍生物的制备方法
FR3037957B1 (fr) * 2015-06-23 2019-01-25 Les Laboratoires Servier Nouveaux derives d'hydroxyester, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
EP3324974B1 (en) * 2015-07-24 2022-06-08 University Of Louisville Research Foundation, Inc. Compounds, compositions, methods for treating diseases, and methods for preparing compounds
CN115279769A (zh) 2019-10-10 2022-11-01 梦欧文科学有限责任公司 N-(4-(1-(2,6-二氟苄基)-5-((二甲基氨基)甲基)-3-(6-甲氧基-3-哒嗪基)-2,4-二氧代-1,2,3,4-四氢噻吩并[2,3-d]嘧啶-6-基)苯基)-n’-甲氧基脲的结晶形式
CN115232146A (zh) * 2022-08-04 2022-10-25 山东大学 一种2-氨基噻吩并[2,3-d]嘧啶类化合物及其制备方法和应用
CN119768172A (zh) 2022-08-18 2025-04-04 米托迪治愈有限责任公司 具有磷酸二酯酶-7抑制活性的治疗剂在治疗和预防与慢性疲劳、衰竭和/或劳累不耐受有关的疾病中的用途

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4008726A1 (de) * 1990-03-19 1991-09-26 Basf Ag Thieno(2,3-d)pyrimidinderivate
US5869486A (en) * 1995-02-24 1999-02-09 Ono Pharmaceutical Co., Ltd. Fused pyrimidines and pyriazines as pharmaceutical compounds
JPH1087492A (ja) * 1996-06-25 1998-04-07 Ono Pharmaceut Co Ltd 一酸化窒素産生阻害剤
DE19644228A1 (de) * 1996-10-24 1998-04-30 Merck Patent Gmbh Thienopyrimidine
US6133271A (en) * 1998-11-19 2000-10-17 Cell Pathways, Inc. Method for inhibiting neoplastic cells and related conditions by exposure thienopyrimidine derivatives
DE19953024A1 (de) * 1999-11-04 2001-05-10 Merck Patent Gmbh Isoxazolderivate als Phosphodiesterase VII-Hemmer
DE19954707A1 (de) * 1999-11-13 2001-05-17 Merck Patent Gmbh Imidazolverbindungen als Phosphodiesterase VII-Hemmer
EP1329454A1 (en) * 2000-09-29 2003-07-23 Nippon Soda Co., Ltd. Thienopyrimidine compounds and their salts and process for preparation of both
EP1193261A1 (en) * 2000-10-02 2002-04-03 Warner-Lambert Company New thiadiazoles and their use as phosphodiesterase-7 inhibitors
EP1401840A4 (en) * 2001-04-30 2007-05-16 Bayer Corp NEW 4-AMINO-5,6-SUBSTITUTED THIOPHENO 2,3 D | PYRIMIDINE
EP1348701A1 (en) * 2002-03-28 2003-10-01 Warner-Lambert Company LLC (2,4-disubstituted-thiazol-5-yl) amine compounds as PDE7 inhibitors

Also Published As

Publication number Publication date
WO2004065391A1 (en) 2004-08-05
ES2289475T3 (es) 2008-02-01
EP1590352B1 (en) 2007-06-27
ATE365742T1 (de) 2007-07-15
US20060229306A1 (en) 2006-10-12
JP2006515604A (ja) 2006-06-01
DE602004007239D1 (de) 2007-08-09
ES2217956A1 (es) 2004-11-01
ES2217956B1 (es) 2006-04-01
DE602004007239T2 (de) 2008-02-28
CN1761671A (zh) 2006-04-19
EP1590352A1 (en) 2005-11-02
US7662814B2 (en) 2010-02-16

Similar Documents

Publication Publication Date Title
CN100582112C (zh) 用作PDE7抑制剂的4-氨基噻吩并[2,3-d]嘧啶-6-甲腈衍生物
EP2464647B1 (en) Azaindazoles as btk kinase modulators and use thereof
CN102361877B (zh) 作为trpa1调节剂的噻吩并嘧啶二酮衍生物
KR101828187B1 (ko) 신규 축합 피리미딘 화합물 또는 그 염
Farghaly et al. Synthesis, anti-HCV, antioxidant, and peroxynitrite inhibitory activity of fused benzosuberone derivatives
ES2291628T3 (es) Compuestos triciclicos a base de tiofeno y composiciones farmaceuticas que comprenden dichos compuestos.
CN113045565A (zh) 新型K-Ras G12C抑制剂
DE60309849T2 (de) Heterozyklische amidderivate mit glykogen-phosphorylase-hemmender wirkung
EP3184521A1 (en) Indazole compounds as fgfr kinase inhibitor, preparation and use thereof
WO1998014449A1 (en) Fused pyrazole derivatives and processes for their preparation
JP2004520273A (ja) Ｐａｒｐの阻害剤として用いるためのチエノ［２，３−ｃ］イソキノリン
SG184766A1 (en) Isothiazolo-pyrimidinedione derivatives as trpa1 modulators
CA2870062A1 (en) Pyrrolopyrazone inhibitors of tankyrase
CA3128846A1 (en) Difluoromethylene compound
CN111655693B (zh) 抑制瞬时型感受器电位a1离子通道
JP2022517085A (ja) ハロゲン化アリルアミン系化合物及びその適用
CN106946760A (zh) 靛玉红衍生物或药学上能接受的盐用于抗肿瘤药物及制备方法
WO2019085894A1 (zh) 一类含氮稠环化合物及其制备方法和用途
WO2005058315A1 (en) Novel heterocyclic compounds as ikk2 inhibitors with anti-hbv activity
EP3534888B1 (en) Substituted bicyclic heteroaryl allosteric modulators of nicotinic acetylcholine receptors
CA3180058A1 (en) Pyrazolo[1,5-a]pyrimidine derivatives having multimodal activity against pain
CA2908084C (en) Rohitukine analogs as cyclin-dependent kinase inhibitors and a process for the preparation thereof
WO2019113179A1 (en) Positive allosteric modulators of the muscarinic acetylcholine receptor m4
CN111978325B (zh) 咪唑并哒嗪类mnk1/mnk2激酶抑制剂及其制备方法和应用
ES2315898T3 (es) Derivados de carbamato de 2h- o 3h-benzo(e)inzadol-1-ilo, su preparacion y su aplicacion en terapeutica.

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
C17 Cessation of patent right
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20100120

Termination date: 20110123