CA2817691C - Metalloenzyme inhibitor compounds - Google Patents

Metalloenzyme inhibitor compounds Download PDF

Info

Publication number
CA2817691C
CA2817691C CA2817691A CA2817691A CA2817691C CA 2817691 C CA2817691 C CA 2817691C CA 2817691 A CA2817691 A CA 2817691A CA 2817691 A CA2817691 A CA 2817691A CA 2817691 C CA2817691 C CA 2817691C
Authority
CA
Canada
Prior art keywords
compound
prodrug
solvate
hydrate
salt
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
CA2817691A
Other languages
English (en)
French (fr)
Other versions
CA2817691A1 (en
Inventor
William J. Hoekstra
Robert J. Schotzinger
Stephen William Rafferty
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.)
Kembi Therapeutics Pty Ltd
Original Assignee
Innocrin Pharmaceuticals 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 Innocrin Pharmaceuticals Inc filed Critical Innocrin Pharmaceuticals Inc
Publication of CA2817691A1 publication Critical patent/CA2817691A1/en
Application granted granted Critical
Publication of CA2817691C publication Critical patent/CA2817691C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/472Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/041,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647Triazoles; Hydrogenated triazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/41921,2,3-Triazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42Oxazoles
    • A61K31/422Oxazoles not condensed and containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/4709Non-condensed quinolines and containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/08Drugs for disorders of the urinary system of the prostate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/02Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/10Anti-acne agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/14Drugs for dermatological disorders for baldness or alopecia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10Antimycotics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/24Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/28Antiandrogens
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/06Heterocyclic 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 only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/10Heterocyclic 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 linked by a carbon chain containing aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/12Heterocyclic 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 linked by a chain containing hetero atoms as chain links
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Neurosurgery (AREA)
  • Reproductive Health (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Endocrinology (AREA)
  • Diabetes (AREA)
  • Urology & Nephrology (AREA)
  • Rheumatology (AREA)
  • Obesity (AREA)
  • Pregnancy & Childbirth (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
CA2817691A 2010-11-13 2011-11-10 Metalloenzyme inhibitor compounds Active CA2817691C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US41339510P 2010-11-13 2010-11-13
US61/413,395 2010-11-13
PCT/US2011/060166 WO2012064943A2 (en) 2010-11-13 2011-11-10 Metalloenzyme inhibitor compounds

Publications (2)

Publication Number Publication Date
CA2817691A1 CA2817691A1 (en) 2012-05-18
CA2817691C true CA2817691C (en) 2020-09-01

Family

ID=46051557

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2817691A Active CA2817691C (en) 2010-11-13 2011-11-10 Metalloenzyme inhibitor compounds

Country Status (13)

Country Link
US (5) US8389543B2 (enExample)
EP (2) EP3483147A1 (enExample)
JP (2) JP5828343B2 (enExample)
KR (2) KR101848077B1 (enExample)
CN (2) CN103339115B (enExample)
AU (2) AU2011326487B2 (enExample)
BR (1) BR112013011830B1 (enExample)
CA (1) CA2817691C (enExample)
EA (1) EA024197B1 (enExample)
ES (1) ES2703498T3 (enExample)
PT (1) PT2638021T (enExample)
TW (1) TWI600647B (enExample)
WO (1) WO2012064943A2 (enExample)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101823275B1 (ko) 2010-08-04 2018-03-08 펠피큐어 파마슈티걸즈 아이엔씨 전립선 암종의 치료를 위한 병용 요법
ES2703498T3 (es) * 2010-11-13 2019-03-11 Innocrin Pharmaceuticals Inc 1-(6,7-Bis(difluorometoxi)naftalen-2-il)-2-metil-1-(1H-1,2,3-triazol-4-il)propan-1-ol como inhibidor de CYP17 para el tratamiento de enfermedades dependientes de andrógenos como el cáncer de próstata
AU2013209516A1 (en) 2012-01-20 2014-08-28 Viamet Pharmaceuticals (NC), Inc. Metalloenzyme inhibitor compounds
US9073875B2 (en) 2012-11-20 2015-07-07 Vertex Pharmaceuticals Incorporated Compounds useful as inhibitors of indoleamine 2,3-dioxygenase
US20160022606A1 (en) * 2013-03-14 2016-01-28 Pellficure Pharmaceuticals Inc. Novel therapy for prostate carcinoma
WO2015070366A1 (en) * 2013-11-12 2015-05-21 Merck Sharp & Dohme Corp. Aryl linked imidazole and triazole derivatives and methods of use thereof for improving the pharmacokinetics of a drug
US9738613B2 (en) 2015-05-18 2017-08-22 National Central University Substituted 1,2,3-triazoles as antitumor agents
ES2970715T3 (es) 2016-12-22 2024-05-30 Prec Pharmaceuticals Inc Composiciones y métodos para inhibir la actividad de la arginasa
EP3570832A4 (en) 2017-01-17 2020-06-10 Board Of Regents, The University Of Texas System NOVEL COMPOUNDS USEFUL AS INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND / OR TRYPTOPHANE DIOXYGENASE
US20210292410A1 (en) * 2017-12-07 2021-09-23 Morphosys Ag Treatment paradigm for an anti-cd19 antibody and venetoclax combination treatment
WO2019113312A1 (en) * 2017-12-08 2019-06-13 Innocrin Pharmaceuticals, Inc. Anticancer compound process
WO2019182743A1 (en) * 2018-03-20 2019-09-26 Innocrin Pharmaceuticals, Inc. Compositions for the treatment of brain tumors
US11046649B2 (en) 2018-07-17 2021-06-29 Board Of Regents, The University Of Texas System Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase
US12357615B2 (en) * 2018-10-11 2025-07-15 Kembi Therapeutics Pty Ltd Compositions for the treatment of brain tumors
CN110256342B (zh) * 2019-07-16 2022-06-07 河南省科学院化学研究所有限公司 一种2-氰基喹啉衍生物的合成方法
CN114957215B (zh) * 2022-01-13 2023-03-21 渤海大学 亚甲基桥连喹啉和1,2,3-三唑双杂环化合物及其制备方法与应用

Family Cites Families (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5087240A (en) 1983-08-18 1992-02-11 Drug Delivery Systems Inc. Transdermal drug patch with conductive fibers
US4921475A (en) 1983-08-18 1990-05-01 Drug Delivery Systems Inc. Transdermal drug patch with microtubes
US4738851A (en) 1985-09-27 1988-04-19 University Of Iowa Research Foundation, Inc. Controlled release ophthalmic gel formulation
US5163899A (en) 1987-03-20 1992-11-17 Drug Delivery Systems Inc. Transdermal drug delivery system
US5312325A (en) 1987-05-28 1994-05-17 Drug Delivery Systems Inc Pulsating transdermal drug delivery system
GB8804164D0 (en) 1988-02-23 1988-03-23 Tucker J M Bandage for administering physiologically active compound
US4882150A (en) 1988-06-03 1989-11-21 Kaufman Herbert E Drug delivery system
US5008110A (en) 1988-11-10 1991-04-16 The Procter & Gamble Company Storage-stable transdermal patch
US5088977A (en) 1988-12-21 1992-02-18 Drug Delivery Systems Inc. Electrical transdermal drug applicator with counteractor and method of drug delivery
US5521222A (en) 1989-09-28 1996-05-28 Alcon Laboratories, Inc. Topical ophthalmic pharmaceutical vehicles
ATE107176T1 (de) 1989-12-04 1994-07-15 Searle & Co System zur transdermalen albuterol applikation.
US5077033A (en) 1990-08-07 1991-12-31 Mediventures Inc. Ophthalmic drug delivery with thermo-irreversible gels of polxoxyalkylene polymer and ionic polysaccharide
EP0495421B1 (en) 1991-01-15 1996-08-21 Alcon Laboratories, Inc. Use of carrageenans in topical ophthalmic compositions
US5352456A (en) 1991-10-10 1994-10-04 Cygnus Therapeutic Systems Device for administering drug transdermally which provides an initial pulse of drug
JPH07502219A (ja) 1991-12-18 1995-03-09 ミネソタ マイニング アンド マニュファクチャリング カンパニー 多重層型バリアー構造体
ATE132381T1 (de) 1992-01-29 1996-01-15 Voelkl Franz Ski Ballspielschläger, insbesondere tennisschläger
IL114193A (en) 1994-06-20 2000-02-29 Teva Pharma Ophthalmic pharmaceutical compositions based on sodium alginate
ES2094688B1 (es) 1994-08-08 1997-08-01 Cusi Lab Manoemulsion del tipo de aceite en agua, util como vehiculo oftalmico y procedimiento para su preparacion.
IT1283911B1 (it) 1996-02-05 1998-05-07 Farmigea Spa Soluzioni oftalmiche viscosizzate con polisaccaridi della gomma di tamarindo
US5800807A (en) 1997-01-29 1998-09-01 Bausch & Lomb Incorporated Ophthalmic compositions including glycerin and propylene glycol
US6261547B1 (en) 1998-04-07 2001-07-17 Alcon Manufacturing, Ltd. Gelling ophthalmic compositions containing xanthan gum
ATE293102T1 (de) * 1998-04-23 2005-04-15 Takeda Pharmaceutical Naphthalene derivate ,ihre herstellung und verwendung
US6197934B1 (en) 1998-05-22 2001-03-06 Collagenesis, Inc. Compound delivery using rapidly dissolving collagen film
EP1274424A4 (en) * 2000-04-12 2003-09-17 Smithkline Beecham Corp CONNECTIONS AND PROCEDURE
EP1434772A4 (en) * 2001-10-12 2005-05-04 Smithkline Beecham Corp CONNECTIONS AND METHODS
PL375353A1 (en) 2002-08-22 2005-11-28 Syngenta Participations Ag Chemical compounds
WO2005007631A1 (en) * 2003-07-10 2005-01-27 Osi Pharmaceuticals, Inc. Naphthylene derivatives as cytochrome p450 inhibitors
US7504424B2 (en) * 2004-07-16 2009-03-17 Schering Corporation Compounds for the treatment of inflammatory disorders
US7488745B2 (en) * 2004-07-16 2009-02-10 Schering Corporation Compounds for the treatment of inflammatory disorders
EP2430920B1 (en) 2007-04-03 2016-11-16 E. I. du Pont de Nemours and Company Substituted benzene fungicides
JP2010523599A (ja) 2007-04-05 2010-07-15 シーメンス メディカル ソリューションズ ユーエスエー インコーポレイテッド クリックケミストリーを使用した炭酸脱水酵素−ixのための分子イメージングプローブの開発
US20110015158A1 (en) * 2007-12-11 2011-01-20 Viamet Pharmaceuticals, Inc. Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties
US20110118219A1 (en) * 2008-03-25 2011-05-19 University Of Maryland, Baltimore Novel prodrugs of c-17-heteroaryl steroidal cyp17 inhibitors/antiandrogens: synthesis, in vitro biological activities, pharmacokinetics and antitumor activity
WO2010032874A1 (ja) * 2008-09-19 2010-03-25 住友化学株式会社 農業用組成物
CA2739251A1 (en) * 2008-10-28 2010-06-03 Biomarin Pharmaceutical Inc. Decahydro-1h-indenoquinolinone and decahydro-3h-cyclopentaphenanthridinone cyp17 inhibitors
WO2011088160A2 (en) * 2010-01-15 2011-07-21 Biomarin Pharmaceutical Inc. Novel cyp17 inhibitors
ES2703498T3 (es) * 2010-11-13 2019-03-11 Innocrin Pharmaceuticals Inc 1-(6,7-Bis(difluorometoxi)naftalen-2-il)-2-metil-1-(1H-1,2,3-triazol-4-il)propan-1-ol como inhibidor de CYP17 para el tratamiento de enfermedades dependientes de andrógenos como el cáncer de próstata

Also Published As

Publication number Publication date
BR112013011830B1 (pt) 2022-03-15
EP2638021B1 (en) 2018-09-26
CA2817691A1 (en) 2012-05-18
CN103339115A (zh) 2013-10-02
BR112013011830A2 (pt) 2020-09-01
TWI600647B (zh) 2017-10-01
EP2638021A2 (en) 2013-09-18
CN103339115B (zh) 2016-08-31
EP3483147A1 (en) 2019-05-15
US8389543B2 (en) 2013-03-05
JP2016094390A (ja) 2016-05-26
US20180221364A1 (en) 2018-08-09
CN106243051B (zh) 2019-03-08
US20130184309A1 (en) 2013-07-18
WO2012064943A2 (en) 2012-05-18
KR20130116286A (ko) 2013-10-23
AU2011326487A1 (en) 2013-06-06
US20140121248A1 (en) 2014-05-01
JP5828343B2 (ja) 2015-12-02
KR101848077B1 (ko) 2018-04-11
CN106243051A (zh) 2016-12-21
EP2638021A4 (en) 2014-05-07
TW201240975A (en) 2012-10-16
PT2638021T (pt) 2019-01-10
AU2017203691A1 (en) 2017-06-15
EA024197B1 (ru) 2016-08-31
US20170143694A1 (en) 2017-05-25
JP2014501717A (ja) 2014-01-23
US20120129886A1 (en) 2012-05-24
US8623892B2 (en) 2014-01-07
AU2011326487B2 (en) 2017-03-02
ES2703498T3 (es) 2019-03-11
WO2012064943A3 (en) 2012-07-05
EA201390704A1 (ru) 2014-04-30
KR20180039185A (ko) 2018-04-17

Similar Documents

Publication Publication Date Title
CA2817691C (en) Metalloenzyme inhibitor compounds
EP2519508B1 (en) Metalloenzyme inhibitor compounds
US9056855B2 (en) Metalloenzyme inhibitor compounds
EP2651905B1 (en) Metalloenzyme inhibitor compounds
EP2751117A2 (en) Metalloenzyme inhibitor compounds

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20161109