CA2920817C - Bicyclic inhibitors of plasma kallikrein - Google Patents

Bicyclic inhibitors of plasma kallikrein Download PDF

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Publication number
CA2920817C
CA2920817C CA2920817A CA2920817A CA2920817C CA 2920817 C CA2920817 C CA 2920817C CA 2920817 A CA2920817 A CA 2920817A CA 2920817 A CA2920817 A CA 2920817A CA 2920817 C CA2920817 C CA 2920817C
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Prior art keywords
group
alkyl
pyridin
independently selected
formula
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CA2920817A
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English (en)
French (fr)
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CA2920817A1 (en
Inventor
Hannah Joy EDWARDS
David Michael Evans
Rebecca Louise DAVIE
David Philip Rooker
Steven John HEWISON
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Kalvista Pharmaceuticals Ltd
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Kalvista Pharmaceuticals Ltd
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Publication of CA2920817A1 publication Critical patent/CA2920817A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5365—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines ortho- or peri-condensed with heterocyclic ring 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
    • 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • 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
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • 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
    • A61P7/10—Antioedematous agents; Diuretics
    • 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
    • A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
    • 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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Cardiology (AREA)
  • Diabetes (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Epidemiology (AREA)
  • Urology & Nephrology (AREA)
  • Rheumatology (AREA)
  • Emergency Medicine (AREA)
  • Obesity (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Endocrinology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pulmonology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA2920817A 2013-08-14 2014-08-14 Bicyclic inhibitors of plasma kallikrein Active CA2920817C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201361865696P 2013-08-14 2013-08-14
GB1314578.4A GB2517908A (en) 2013-08-14 2013-08-14 Bicyclic inhibitors
US61/865,696 2013-08-14
GB1314578.4 2013-08-14
PCT/GB2014/052511 WO2015022547A1 (en) 2013-08-14 2014-08-14 Bicyclic inhibitors

Publications (2)

Publication Number Publication Date
CA2920817A1 CA2920817A1 (en) 2015-02-19
CA2920817C true CA2920817C (en) 2022-04-05

Family

ID=49262178

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2920817A Active CA2920817C (en) 2013-08-14 2014-08-14 Bicyclic inhibitors of plasma kallikrein

Country Status (12)

Country Link
US (1) US9738641B2 (enExample)
EP (1) EP3033332B8 (enExample)
JP (1) JP6527148B2 (enExample)
CN (1) CN105683175B (enExample)
BR (1) BR112016003040B1 (enExample)
CA (1) CA2920817C (enExample)
ES (1) ES2691084T3 (enExample)
GB (1) GB2517908A (enExample)
MX (1) MX362806B (enExample)
PL (1) PL3033332T3 (enExample)
RU (1) RU2672582C2 (enExample)
WO (1) WO2015022547A1 (enExample)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI636047B (zh) 2013-08-14 2018-09-21 英商卡爾維斯塔製藥有限公司 雜環衍生物
WO2015171527A1 (en) 2014-05-05 2015-11-12 Global Blood Therapeutics, Inc. Pyrazolopyridine pyrazolopyrimidine and related compounds
GB201421083D0 (en) 2014-11-27 2015-01-14 Kalvista Pharmaceuticals Ltd Enzyme inhibitors
GB201421085D0 (en) 2014-11-27 2015-01-14 Kalvista Pharmaceuticals Ltd New enzyme inhibitors
ME03794B (me) 2016-05-31 2021-04-20 Kalvista Pharmaceuticals Ltd Derivati pirazola kao inhibitori kalikreina plazme
GB201609607D0 (en) 2016-06-01 2016-07-13 Kalvista Pharmaceuticals Ltd Polymorphs of N-(3-Fluoro-4-methoxypyridin-2-yl)methyl)-3-(methoxymethyl)-1-({4-((2-oxopy ridin-1-yl)methyl)phenyl}methyl)pyrazole-4-carboxamide and salts
GB201609603D0 (en) 2016-06-01 2016-07-13 Kalvista Pharmaceuticals Ltd Polymorphs of N-[(6-cyano-2-fluoro-3-methoxyphenyl)Methyl]-3-(methoxymethyl)-1-({4-[(2-ox opyridin-1-YL)Methyl]phenyl}methyl)pyrazole-4-carboxamide
US11554104B2 (en) * 2017-08-18 2023-01-17 The Schepens Eye Research Institute, Inc. Compositions for the treatment of dry eye and methods of use thereof
GB201719881D0 (en) 2017-11-29 2018-01-10 Kalvista Pharmaceuticals Ltd Solid forms of plasma kallikrein inhibitor and salts thereof
PL3716952T3 (pl) 2017-11-29 2022-05-02 Kalvista Pharmaceuticals Limited Postacie dawkowania zawierające inhibitor kalikreiny osoczowej
WO2021028645A1 (en) 2019-08-09 2021-02-18 Kalvista Pharmaceuticals Limited Plasma kallikrein inhibitors
CN114269430A (zh) * 2019-08-21 2022-04-01 卡尔维斯塔制药有限公司 酶抑制剂
CA3189771A1 (en) 2020-07-22 2022-01-27 Janssen Pharmaceutica Nv Compounds useful as factor xia inhibitors
WO2025153806A1 (en) 2024-01-15 2025-07-24 Kalvista Pharmaceuticals Limited Methods for determining amidolytic activity

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5187157A (en) 1987-06-05 1993-02-16 Du Pont Merck Pharmaceutical Company Peptide boronic acid inhibitors of trypsin-like proteases
GB9019558D0 (en) 1990-09-07 1990-10-24 Szelke Michael Enzyme inhibitors
SE9301911D0 (sv) 1993-06-03 1993-06-03 Ab Astra New peptide derivatives
US5589467A (en) 1993-09-17 1996-12-31 Novo Nordisk A/S 2,5',N6-trisubstituted adenosine derivatives
WO1996031504A1 (en) * 1995-04-04 1996-10-10 Merck & Co., Inc. Thrombin inhibitors
US5786328A (en) 1995-06-05 1998-07-28 Genentech, Inc. Use of kunitz type plasma kallikrein inhibitors
JP3957023B2 (ja) * 1997-11-12 2007-08-08 三菱化学株式会社 プリン誘導体及びそれを有効成分として含む医薬
GB0205527D0 (en) * 2002-03-08 2002-04-24 Ferring Bv Inhibitors
NZ592039A (en) 2003-08-27 2013-03-28 Ophthotech Corp Combination therapy for the treatment of ocular neovascular disorders
US7429604B2 (en) 2004-06-15 2008-09-30 Bristol Myers Squibb Company Six-membered heterocycles useful as serine protease inhibitors
DK1784402T3 (da) * 2004-09-03 2011-11-14 Yuhan Corp Pyrrolo[3,2-c]pyridinderivater samt fremgangsmåder til deres fremstilling
KR101142363B1 (ko) * 2005-06-27 2012-05-21 주식회사유한양행 피롤로피리딘 유도체를 포함하는 항암제 조성물
JP5225098B2 (ja) * 2005-12-14 2013-07-03 ブリストル−マイヤーズ スクイブ カンパニー 第ＸＩａ因子インヒビターとしてのアリールプロピオンアミド、アリールアクリルアミド、アリールプロピンアミド、またはアリールメチルウレアアナログ
EP2051707B1 (en) 2006-07-31 2013-07-17 Activesite Pharmaceuticals, Inc. Inhibitors of plasma kallikrein
DE102006050672A1 (de) 2006-10-24 2008-04-30 Curacyte Discovery Gmbh Hemmstoffe des Plasmins und des Plasmakallikreins
GB0910003D0 (en) 2009-06-11 2009-07-22 Univ Leuven Kath Novel compounds for the treatment of neurodegenerative diseases
JP2013121919A (ja) 2010-03-25 2013-06-20 Astellas Pharma Inc 血漿カリクレイン阻害剤
ES2483802T3 (es) 2010-07-07 2014-08-07 The Medicines Company (Leipzig) Gmbh Inhibidores de serina proteasa
US9290485B2 (en) 2010-08-04 2016-03-22 Novartis Ag N-((6-amino-pyridin-3-yl)methyl)-heteroaryl-carboxamides
US20140378474A1 (en) * 2012-01-27 2014-12-25 Novartis Ag 5-membered heteroarylcarboxamide derivatives as plasma kallikrein inhibitors
US20140350034A1 (en) * 2012-01-27 2014-11-27 Novartis Ag Aminopyridine derivatives as plasma kallikrein inhibitors
GB201300304D0 (en) 2013-01-08 2013-02-20 Kalvista Pharmaceuticals Ltd Benzylamine derivatives
HRP20221373T1 (hr) 2014-03-07 2023-01-06 Biocryst Pharmaceuticals, Inc. Supstituirani pirazoli kao inhibitori kalikreina u ljudskoj plazmi
WO2015171527A1 (en) 2014-05-05 2015-11-12 Global Blood Therapeutics, Inc. Pyrazolopyridine pyrazolopyrimidine and related compounds
WO2015171526A2 (en) 2014-05-05 2015-11-12 Global Blood Therapeutics, Inc. Tricyclic pyrazolopyridine compounds
KR102286305B1 (ko) 2014-07-16 2021-08-09 라이프에스씨아이 파마슈티컬스, 인크. 치료적 억제 화합물

Also Published As

Publication number Publication date
EP3033332B8 (en) 2018-10-31
RU2016108762A (ru) 2017-09-19
EP3033332B1 (en) 2018-09-19
RU2016108762A3 (enExample) 2018-04-27
GB2517908A (en) 2015-03-11
WO2015022547A1 (en) 2015-02-19
BR112016003040B1 (pt) 2022-01-25
ES2691084T3 (es) 2018-11-23
MX362806B (es) 2019-02-14
RU2672582C2 (ru) 2018-11-16
JP2016528245A (ja) 2016-09-15
MX2016001865A (es) 2016-05-24
GB201314578D0 (en) 2013-09-25
CN105683175A (zh) 2016-06-15
US20160185773A1 (en) 2016-06-30
EP3033332A1 (en) 2016-06-22
CN105683175B (zh) 2018-04-03
CA2920817A1 (en) 2015-02-19
JP6527148B2 (ja) 2019-06-05
US9738641B2 (en) 2017-08-22
PL3033332T3 (pl) 2019-02-28
BR112016003040A2 (enExample) 2017-08-01

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