CA2433879A1 - C-terminal modified oxamyl dipeptides as inhibitors of the ice/ced-3 family of cysteine proteases - Google Patents

C-terminal modified oxamyl dipeptides as inhibitors of the ice/ced-3 family of cysteine proteases Download PDF

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Publication number
CA2433879A1
CA2433879A1 CA002433879A CA2433879A CA2433879A1 CA 2433879 A1 CA2433879 A1 CA 2433879A1 CA 002433879 A CA002433879 A CA 002433879A CA 2433879 A CA2433879 A CA 2433879A CA 2433879 A1 CA2433879 A1 CA 2433879A1
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Canada
Prior art keywords
phenyl
substituted
naphthyl
cycloalkyl
alkyl
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Abandoned
Application number
CA002433879A
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English (en)
French (fr)
Inventor
Donald S. Karanewsky
Robert J. Ternansky
Steven D. Linton
Thang Dinh
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.)
Idun Pharmaceuticals Inc
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Individual
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Publication of CA2433879A1 publication Critical patent/CA2433879A1/en
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182Radicals derived from carboxylic acids
    • C07D295/185Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • 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
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    • AHUMAN NECESSITIES
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    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
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    • AHUMAN NECESSITIES
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    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
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    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
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    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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    • A61P31/14Antivirals for RNA viruses
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    • A61P7/04Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
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    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06Antianaemics
    • AHUMAN NECESSITIES
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02Carboxylic 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
    • C07C237/22Carboxylic 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
    • CCHEMISTRY; METALLURGY
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/44Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/48Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C317/50Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/30Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32Esters thereof
    • C07F9/3258Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/3264Esters with hydroxyalkyl compounds
    • CCHEMISTRY; METALLURGY
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    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated
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    • C07C2602/00Systems containing two condensed rings
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    • C07C2602/04One of the condensed rings being a six-membered aromatic ring
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    • C07C2602/04One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/56Ring systems containing bridged rings
    • C07C2603/58Ring systems containing bridged rings containing three rings
    • C07C2603/70Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74Adamantanes

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  • Animal Behavior & Ethology (AREA)
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  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Virology (AREA)
  • Diabetes (AREA)
  • Neurology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
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  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Immunology (AREA)
  • Hematology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Endocrinology (AREA)
  • Dermatology (AREA)
  • Urology & Nephrology (AREA)
  • Biochemistry (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Biotechnology (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
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CA002433879A 2001-01-16 2002-01-16 C-terminal modified oxamyl dipeptides as inhibitors of the ice/ced-3 family of cysteine proteases Abandoned CA2433879A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/765,105 2001-01-16
US09/765,105 US7053056B2 (en) 1998-07-02 2001-01-16 C-terminal modified oxamyl dipeptides as inhibitors of the ICE/ced-3 family of cysteine proteases
PCT/US2002/001538 WO2002057298A2 (en) 2001-01-16 2002-01-16 C-terminal modified oxamyl dipeptides as inhibitors of the ice/ced-3 family of cysteine proteases

Publications (1)

Publication Number Publication Date
CA2433879A1 true CA2433879A1 (en) 2002-07-25

Family

ID=25072661

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002433879A Abandoned CA2433879A1 (en) 2001-01-16 2002-01-16 C-terminal modified oxamyl dipeptides as inhibitors of the ice/ced-3 family of cysteine proteases

Country Status (6)

Country Link
US (2) US7053056B2 (https=)
EP (1) EP1351975A2 (https=)
JP (1) JP2004521107A (https=)
CN (1) CN1283656C (https=)
CA (1) CA2433879A1 (https=)
WO (1) WO2002057298A2 (https=)

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US6184210B1 (en) * 1997-10-10 2001-02-06 Cytovia, Inc. Dipeptide apoptosis inhibitors and the use thereof
EP1718639A2 (en) 2004-02-27 2006-11-08 Vertex Pharmaceuticals Incorporated Caspase inhibitors and uses thereof
KR101125932B1 (ko) * 2006-12-06 2012-03-22 아이디유엔 파마슈티칼즈, 인코포레이티드 (3s)-3-[n-(n'-(2-tert-부틸페닐)옥사밀)알라니닐]아미노-5-(2',3',5',6'-테트라플루오로페녹시)-4-옥소펜탄산의 결정 형태
CA2737774A1 (en) 2008-09-19 2010-03-25 Henry Ford Health System Methods, systems, and compositions for calpain inhibition
WO2012021800A2 (en) * 2010-08-13 2012-02-16 Banyan Biomarkers Caspase inhibitors as therapeutics for neural and organ injury and imaging
US9539050B2 (en) * 2011-04-12 2017-01-10 Covidien Lp System and method for process monitoring and intelligent shut-off
ES2751652T3 (es) 2014-05-12 2020-04-01 Conatus Pharmaceuticals Inc Tratamiento con inhibidor de caspasa emricasan de las complicaciones por las enfermedades hepáticas crónicas
MX378266B (es) 2014-10-06 2025-03-10 Lighthouse Pharmaceuticals Inc Inhibidores de gingipaina de lisina.
EP3265440A1 (en) 2015-03-06 2018-01-10 Concert Pharmaceuticals Inc. Deuterated emricasan
WO2017079566A1 (en) 2015-11-05 2017-05-11 Conatus Pharmaceuticals, Inc. Caspase inhibitors for use in the treatment of liver cancer
CN108602787A (zh) 2015-11-09 2018-09-28 库特克希米公司 精氨酸牙龈卟啉菌蛋白酶的抑制剂
JP2019500397A (ja) 2015-12-31 2019-01-10 クオナトウス ファーマシューティカルズ,インコーポレイテッド カスパーゼ阻害剤を肝疾患の治療に使用する方法
CN109983012B (zh) 2016-09-16 2023-12-01 莱特豪斯制药公司 赖氨酸牙龈蛋白酶的酮抑制剂
RU2019113150A (ru) 2016-10-05 2020-11-06 Новартис Аг Комбинация композиций, содержащих агонисты fxr, предназначенная для лечения или предупреждения фиброзирующего, цирротического заболевания или нарушения
WO2022123062A1 (en) 2020-12-11 2022-06-16 INSERM (Institut National de la Santé et de la Recherche Médicale) Blocking caspase and/or fasl for preventing fatal outcome in covid-19 patients

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US6204261B1 (en) 1995-12-20 2001-03-20 Vertex Pharmaceuticals Incorporated Inhibitors of interleukin-1β Converting enzyme inhibitors
EP0618223A3 (en) 1993-03-08 1996-06-12 Sandoz Ltd Peptides, the release of Interleukin 1-Bêta, useful as anti-inflammatory agents.
TW494094B (en) 1993-04-29 2002-07-11 Vertex Pharma Peptide analogs as irreversible interleukin-1β protease inhibitors and pharmaceutical compositions comprising the same
US5869519A (en) 1996-12-16 1999-02-09 Idun Pharmaceuticals, Inc. C-terminal modified (n-substituted)-2-indolyl dipeptides as inhibitors of the ICE/ced-3 family of cysteine proteases
EP0929311B8 (en) 1996-09-12 2006-02-01 Idun Pharmaceuticals, Inc. INHIBITION OF APOPTOSIS USING INTERLEUKIN-1 beta-CONVERTING ENZYME (ICE)/CED-3 FAMILY INHIBITORS
US5968927A (en) 1996-09-20 1999-10-19 Idun Pharmaceuticals, Inc. Tricyclic compounds for the inhibition of the ICE/ced-3 protease family of enzymes
US5877197A (en) 1996-12-16 1999-03-02 Karanewsky; Donald S. C-terminal modified (N-substituted)-2-indolyl dipeptides as inhibitors of the ICE/ced-3 family of cysteine proteases
US6184244B1 (en) 1996-12-16 2001-02-06 Idun Pharmaceuticals, Inc. C-terminal modified (N-substituted)-2-indolyl dipeptides as inhibitors of the ICE/ced-3 family of cysteine proteases
FR2766188B1 (fr) 1997-07-15 2000-02-11 Hoechst Marion Roussel Inc Nouveau procede de preparation de derives amines d'alkyloxy furanone, composes issus de ce procede et utilisation de ces composes
US6544951B2 (en) 1998-07-02 2003-04-08 Idun Pharmaceuticals, Inc. C-terminal modified oxamyl dipeptides as inhibitors of the ICE/ced-3 family of cysteine proteases
US6197750B1 (en) 1998-07-02 2001-03-06 Idun Pharmaceuticals, Inc. C-terminal modified oxamyl dipeptides as inhibitors of the ICE/ced-3 family of cysteine proteases
US6242422B1 (en) 1998-10-22 2001-06-05 Idun Pharmacueticals, Inc. (Substituted)Acyl dipeptidyl inhibitors of the ice/ced-3 family of cysteine proteases
US6515173B1 (en) 2000-01-13 2003-02-04 Idun Pharmaceuticals, Inc. Inhibitors of the ICE/ced-3 family of cysteine proteases
CA2402128A1 (en) 2000-04-24 2001-11-01 Vertex Pharmaceuticals Incorporated Process and intermediates for making substituted aspartic acid acetals

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Publication number Publication date
US20020042376A1 (en) 2002-04-11
CN1525978A (zh) 2004-09-01
US7183260B2 (en) 2007-02-27
CN1283656C (zh) 2006-11-08
WO2002057298A3 (en) 2003-05-15
JP2004521107A (ja) 2004-07-15
US20050020504A1 (en) 2005-01-27
WO2002057298A2 (en) 2002-07-25
US7053056B2 (en) 2006-05-30
EP1351975A2 (en) 2003-10-15

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