CA2878319C - Polymorphs of n-[(r)-1-[(s)-1-(4-aminomethyl-benzylcarbamoyl)-2-phenyl-ethylcarbamoyl]-2-(4-ethoxy-phenyl)-ethyl]-benzamide hydrochloride - Google Patents

Polymorphs of n-[(r)-1-[(s)-1-(4-aminomethyl-benzylcarbamoyl)-2-phenyl-ethylcarbamoyl]-2-(4-ethoxy-phenyl)-ethyl]-benzamide hydrochloride Download PDF

Info

Publication number
CA2878319C
CA2878319C CA2878319A CA2878319A CA2878319C CA 2878319 C CA2878319 C CA 2878319C CA 2878319 A CA2878319 A CA 2878319A CA 2878319 A CA2878319 A CA 2878319A CA 2878319 C CA2878319 C CA 2878319C
Authority
CA
Canada
Prior art keywords
phenyl
solid form
ethyl
plasma kallikrein
ethoxy
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.)
Active
Application number
CA2878319A
Other languages
English (en)
French (fr)
Other versions
CA2878319A1 (en
Inventor
Julian Scott Northen
John Mykytiuk
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.)
Kalvista Pharmaceuticals Ltd
Original Assignee
Kalvista Pharmaceuticals Ltd
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 Kalvista Pharmaceuticals Ltd filed Critical Kalvista Pharmaceuticals Ltd
Publication of CA2878319A1 publication Critical patent/CA2878319A1/en
Application granted granted Critical
Publication of CA2878319C publication Critical patent/CA2878319C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • 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
    • 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
    • A61P9/10—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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/22—Separation; Purification; Stabilisation; Use of additives
    • C07C231/24—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • 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
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Rheumatology (AREA)
  • Oncology (AREA)
  • Biomedical Technology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pain & Pain Management (AREA)
  • Vascular Medicine (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Communicable Diseases (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pulmonology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
CA2878319A 2012-07-06 2013-07-05 Polymorphs of n-[(r)-1-[(s)-1-(4-aminomethyl-benzylcarbamoyl)-2-phenyl-ethylcarbamoyl]-2-(4-ethoxy-phenyl)-ethyl]-benzamide hydrochloride Active CA2878319C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201261668543P 2012-07-06 2012-07-06
GB1212081.2 2012-07-06
GB201212081A GB201212081D0 (en) 2012-07-06 2012-07-06 New polymorph
US61/668,543 2012-07-06
PCT/GB2013/051781 WO2014006414A1 (en) 2012-07-06 2013-07-05 Polymorphs of|n-[(r)-1 -[(s)-1-(4-aminomethyl-benzylcarbamoyl)-2-phenyl-ethylcarbamoy l]-2-(4-e|thoxy-phenyl)-ethyl]-benzamide hydrochloride

Publications (2)

Publication Number Publication Date
CA2878319A1 CA2878319A1 (en) 2014-01-09
CA2878319C true CA2878319C (en) 2021-02-09

Family

ID=46766283

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2878319A Active CA2878319C (en) 2012-07-06 2013-07-05 Polymorphs of n-[(r)-1-[(s)-1-(4-aminomethyl-benzylcarbamoyl)-2-phenyl-ethylcarbamoyl]-2-(4-ethoxy-phenyl)-ethyl]-benzamide hydrochloride

Country Status (10)

Country Link
US (1) US9512065B2 (enExample)
EP (1) EP2870137B8 (enExample)
JP (1) JP6367187B2 (enExample)
CA (1) CA2878319C (enExample)
ES (1) ES2679370T3 (enExample)
GB (1) GB201212081D0 (enExample)
HU (1) HUE039775T2 (enExample)
PL (1) PL2870137T3 (enExample)
TR (1) TR201809681T4 (enExample)
WO (1) WO2014006414A1 (enExample)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2510407A (en) * 2013-02-04 2014-08-06 Kalvista Pharmaceuticals Ltd Aqueous suspensions of kallikrein inhibitors for parenteral administration
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
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
EP3426685A1 (en) 2016-03-10 2019-01-16 Oxurion NV Posterior ocular fibrosis inhibition by antagonizing placental growth factor
ME03794B (me) 2016-05-31 2021-04-20 Kalvista Pharmaceuticals Ltd Derivati pirazola kao inhibitori kalikreina plazme
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
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
JOP20190144A1 (ar) 2016-12-16 2019-06-16 Janssen Pharmaceutica Nv إيميدازو بيرولو بيريدين كمثبطات لعائلة jak الخاصة بإنزيمات الكيناز
MX2022004474A (es) 2016-12-16 2023-08-15 Janssen Pharmaceutica Nv Inhibidores de moléculas pequeñas de la familia de quinasas jak.
CN110234351A (zh) 2017-01-30 2019-09-13 詹森生物科技公司 用于治疗活动性银屑病关节炎的抗tnf抗体、组合物和方法
KR20240038148A (ko) 2017-02-07 2024-03-22 얀센 바이오테크 인코포레이티드 활성 강직성 척추염의 치료를 위한 항-tnf 항체, 조성물, 및 방법
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
TW202016110A (zh) 2018-06-15 2020-05-01 比利時商健生藥品公司 Ｊａｋ激酶家族之小分子抑制劑
UY38438A (es) 2018-11-02 2020-05-29 Biocryst Pharm Inc Sales cristalinas de un inhibidor de calicreína plasmática
EP3972690A4 (en) 2019-05-23 2023-07-05 Janssen Biotech, Inc. METHOD OF TREATMENT OF INFLAMMATORY BOWEL DISEASE USING COMBINATION THERAPY OF ANTIBODIES TO IL-23 AND TNF-ALPHA
WO2021028645A1 (en) 2019-08-09 2021-02-18 Kalvista Pharmaceuticals Limited Plasma kallikrein inhibitors
GB2591730A (en) 2019-12-09 2021-08-11 Kalvista Pharmaceuticals Ltd New polymorphs
GB201918994D0 (en) 2019-12-20 2020-02-05 Kalvista Pharmaceuticals Ltd Treatments of diabetic macular edema and impaired visual acuity
CA3183927A1 (en) 2020-05-21 2021-11-25 Janssen Biotech, Inc. Method of treating inflammatory bowel disease with a combination therapy of antibodies to il-23 and tnf alpha
US12390451B2 (en) 2021-03-11 2025-08-19 Janssen Pharmaceutica Nv Small molecule inhibitor of the JAK family of kinases

Family Cites Families (24)

* 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
IT1223401B (it) * 1987-12-02 1990-09-19 Montedison Spa Poliesteri aromatici liquido cristallini termotropici
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
ZA951617B (en) * 1994-03-04 1997-02-27 Lilly Co Eli Antithrombotic agents.
US5914319A (en) * 1995-02-27 1999-06-22 Eli Lilly And Company Antithrombotic agents
JP4179878B2 (ja) * 2001-02-02 2008-11-12 中外製薬株式会社 ペプチド誘導体
GB0205527D0 (en) 2002-03-08 2002-04-24 Ferring Bv Inhibitors
DE10301300B4 (de) * 2003-01-15 2009-07-16 Curacyte Chemistry Gmbh Verwendung von acylierten 4-Amidino- und 4-Guanidinobenzylaminen zur Inhibierung von Plasmakallikrein
NZ592039A (en) 2003-08-27 2013-03-28 Ophthotech Corp Combination therapy for the treatment of ocular neovascular disorders
EP1730104A1 (en) * 2004-04-02 2006-12-13 Glaxo Group Limited Chemical process and new crystalline form
US7453002B2 (en) * 2004-06-15 2008-11-18 Bristol-Myers Squibb Company Five-membered heterocycles useful as serine protease inhibitors
ATE429415T1 (de) * 2004-11-30 2009-05-15 Mallinckrodt Inc Verfahren zur kristallisierung von benzphetamin
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
US8609866B2 (en) 2009-12-18 2013-12-17 Activesite Pharmaceuticals, Inc. Prodrugs of inhibitors of plasma kallikrein
WO2011094496A2 (en) 2010-01-28 2011-08-04 The Medicines Company Trypsin-like serine protease inhibitors, and their preparation and use
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
EP2697196A1 (en) 2011-04-13 2014-02-19 Activesite Pharmaceuticals, Inc. Prodrugs of inhibitors of plasma kallikrein
GB2494851A (en) * 2011-07-07 2013-03-27 Kalvista Pharmaceuticals Ltd Plasma kallikrein inhibitors

Also Published As

Publication number Publication date
JP6367187B2 (ja) 2018-08-01
PL2870137T3 (pl) 2018-12-31
TR201809681T4 (tr) 2018-07-23
EP2870137A1 (en) 2015-05-13
WO2014006414A1 (en) 2014-01-09
US9512065B2 (en) 2016-12-06
US20150191421A1 (en) 2015-07-09
GB201212081D0 (en) 2012-08-22
EP2870137B8 (en) 2018-07-18
CA2878319A1 (en) 2014-01-09
JP2015528798A (ja) 2015-10-01
HUE039775T2 (hu) 2019-02-28
EP2870137B1 (en) 2018-05-16
ES2679370T3 (es) 2018-08-24

Similar Documents

Publication Publication Date Title
US9512065B2 (en) Polymorphs of N-[(R)-1-[(S)-1-(4-aminomethyl-benzylcarbamoyl)-2-phenyl-ethylcarbamoyl]-2-(4-ethoxy-phenyl)-ethyl]-benzamide hydrochloride
US11739068B2 (en) Polymorphs of N-[(3-fluoro-4-methoxypyridin-2-yl)methyl]-3-(methoxymethyl)-1-({4-[(2-oxopyridin-1-yl)methyl]phenyl}methyl)pyrazole-4-carboxamide and salts thereof
AU2012280064B2 (en) Benzylamine derivatives as inhibitors of plasma kallikrein
US10752607B2 (en) Polymorphs of N-[(6-cyano-2-fluoro)-3-methoxyphenyl)methyl]-3-(methoxymethyl)-1-({4-[(2-oxopyridin-1-yl)methyl]phenyl}methyl)pyrazole-4-carboxamide as kallikrein inhibitors
US20200325116A1 (en) Solid forms of a plasma kallikrein inhibitor and salts thereof
US20200317639A1 (en) Polymorphs of n-[(2,6-difluoro-3-methoxyphenyl)methyl]-3-(methoxymethyl)-1-({4-[(2-oxopyridin-1yl)methyl]phenyl}methyl)pyrazole-4-carboxamide
GB2591730A (en) New polymorphs
JP2009503027A (ja) アルツハイマー病ｉｉの治療のための置換エタン−１，２−ジアミン
HK40088831A (en) Polymorphs of n-[(3-fluoro-4-methoxypyridin-2-yl)methyl]-3-(methoxymethyl)-1-({4-[2-oxopyridin-1-yl)methyl]phenyl}methyl)pyrazole-4-carboxamide as kallikrein inhibitors
NZ788605A (en) Polymorphs of n-[(3-fluoro-4-methoxypyridin-2-yl)methyl]-3-(methoxymethyl)-1-({4-[(2-oxopyridin-1-yl)methyl]phenyl}methyl)pyrazole-4-carboxamide and salts thereof
HK40005630B (en) Polymorphs of n-[(3-fluoro-4-methoxypyridin-2-yl)methyl]-3-(methoxymethyl)-1-({4-[2-oxopyridin-1-yl)methyl]phenyl}methyl)pyrazole-4-carboxamide as kallikrein inhibitors
HK40005630A (en) Polymorphs of n-[(3-fluoro-4-methoxypyridin-2-yl)methyl]-3-(methoxymethyl)-1-({4-[2-oxopyridin-1-yl)methyl]phenyl}methyl)pyrazole-4-carboxamide as kallikrein inhibitors

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20180626

H11 Ip right ceased following rejected request for revival

Free format text: ST27 STATUS EVENT CODE: T-6-6-H10-H11-H101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: TIME LIMIT FOR REVERSAL EXPIRED

Effective date: 20250106