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ES2132096T3 - Pseudopeptidos y peptidos caracterizados por una parte metilo cetona sustituida en la terminacion c como inhibidores de tiol proteasa. - Google Patents

Pseudopeptidos y peptidos caracterizados por una parte metilo cetona sustituida en la terminacion c como inhibidores de tiol proteasa.

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Publication number
ES2132096T3
ES2132096T3 ES92111129T ES92111129T ES2132096T3 ES 2132096 T3 ES2132096 T3 ES 2132096T3 ES 92111129 T ES92111129 T ES 92111129T ES 92111129 T ES92111129 T ES 92111129T ES 2132096 T3 ES2132096 T3 ES 2132096T3
Authority
ES
Spain
Prior art keywords
protease
tiol
pseudopeptides
inhibitors
termination
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 - Lifetime
Application number
ES92111129T
Other languages
English (en)
Inventor
Ryoichi Ando
Naoko Ando
Hirokazu Masuda
Yasuhiro Morinaka
Chizuko Takahashi
Yoshikuni Tamao
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.)
Mitsubishi Chemical Corp
Original Assignee
Mitsubishi Chemical Corp
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Filing date
Publication date
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Application granted granted Critical
Publication of ES2132096T3 publication Critical patent/ES2132096T3/es
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Expired - Lifetime legal-status Critical Current

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    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06043—Leu-amino acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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Abstract

NUEVO DERIVADO DE ACETONA (I) QUE POSEE UNA POTENTE ACTIVIDAD INHIBIDORA CONTRA LA PROTEASA TIOL, TAL COMO LA PAPAINA, CATEPSINA B, CATEPSINA H, CATEPSINA L, CALPAINA O SIMILARES CON EXCELENTES PROPIEDADES RESPECTO A LA ABSORBENCIA ORAL, TRANSFERENCIA DE TEJIDO Y PERMEABILIDAD DE MEMBRANA CELULAR Y ES CLINICAMENTE UTIL EN EL TRATAMIENTO DE VARIAS ENFERMEDADES, TALES COMO LA DISTROFIA MUSCULAR, AMIOTROFIA. TAMBIEN SE PROPORCIONA UN PROCESO PARA PRODUCIR EL COMPUESTO (I) Y UN COMPUESTO FARMACEUTICO QUE CONTIENE EL MISMO.
ES92111129T 1991-07-01 1992-07-01 Pseudopeptidos y peptidos caracterizados por una parte metilo cetona sustituida en la terminacion c como inhibidores de tiol proteasa. Expired - Lifetime ES2132096T3 (es)

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JP16067491 1991-07-01
JP27790591 1991-10-24
JP34366891 1991-12-25

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JP (1) JP3190431B2 (es)
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AT (1) ATE179974T1 (es)
CA (1) CA2072834A1 (es)
DE (1) DE69229151T2 (es)
DK (1) DK0525420T3 (es)
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GR (1) GR3030837T3 (es)
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Families Citing this family (57)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6008217A (en) * 1995-12-20 1999-12-28 Vertex Pharmaceuticals Incorporated Inhibitors of interleukin-1β converting enzyme
US6204261B1 (en) 1995-12-20 2001-03-20 Vertex Pharmaceuticals Incorporated Inhibitors of interleukin-1β Converting enzyme inhibitors
US5874424A (en) * 1995-12-20 1999-02-23 Vertex Pharmaceuticals Incorporated Inhibitors of interleukin-1β converting enzyme
EP0649443A4 (en) * 1992-06-30 1995-11-08 Legomer Partners Lp MATERIALS DERIVED FROM OXAZOLON.
ES2124281T3 (es) * 1992-12-25 1999-02-01 Mitsubishi Chem Corp Derivados de alfa-aminocetonas.
CA2111930A1 (en) * 1992-12-25 1994-06-26 Ryoichi Ando Aminoketone derivatives
JP2848232B2 (ja) * 1993-02-19 1999-01-20 武田薬品工業株式会社 アルデヒド誘導体
US5714484A (en) * 1993-12-08 1998-02-03 Prototek, Inc. α-(1,3-dicarbonylenol ether) methyl ketones as cysteine protease inhibitors
US5486623A (en) 1993-12-08 1996-01-23 Prototek, Inc. Cysteine protease inhibitors containing heterocyclic leaving groups
US5501969A (en) 1994-03-08 1996-03-26 Human Genome Sciences, Inc. Human osteoclast-derived cathepsin
US5847135A (en) * 1994-06-17 1998-12-08 Vertex Pharmaceuticals, Incorporated Inhibitors of interleukin-1β converting enzyme
US6420522B1 (en) 1995-06-05 2002-07-16 Vertex Pharmaceuticals Incorporated Inhibitors of interleukin-1β converting enzyme
US5756466A (en) * 1994-06-17 1998-05-26 Vertex Pharmaceuticals, Inc. Inhibitors of interleukin-1β converting enzyme
US5716929A (en) * 1994-06-17 1998-02-10 Vertex Pharmaceuticals, Inc. Inhibitors of interleukin-1β converting enzyme
WO1996016981A2 (en) * 1994-12-02 1996-06-06 Fujisawa Pharmaceutical Co., Ltd. Peptide compounds for prevention and/or treatment of no-mediated diseases
US5691368A (en) * 1995-01-11 1997-11-25 Hoechst Marion Roussel, Inc. Substituted oxazolidine calpain and/or cathepsin B inhibitors
TW394764B (en) * 1995-02-14 2000-06-21 Mitsubishi Chemcal Corp Oxygen-containing heterocyclic derivatives
US6586466B2 (en) 1995-10-30 2003-07-01 Smithkline Beecham Corporation Carbohydrazide-protease inhibitors
SK56798A3 (en) 1995-10-30 1998-12-02 Smithkline Beecham Corp Protease inhibitors, pharmaceutical composition containing them and their use
US5843904A (en) * 1995-12-20 1998-12-01 Vertex Pharmaceuticals, Inc. Inhibitors of interleukin-1βconverting enzyme
WO1997049668A1 (en) * 1996-06-13 1997-12-31 Smithkline Beecham Corporation Inhibitiors of cysteine protease
WO1998001130A1 (fr) * 1996-07-10 1998-01-15 Mitsubishi Chemical Corporation Agents de traitement des maladies ischemiques
WO1998001129A1 (fr) * 1996-07-10 1998-01-15 Mitsubishi Chemical Corporation Agents de prevention ou de traitement de maladies neurodegeneratives
AR013079A1 (es) * 1997-05-06 2000-12-13 Smithkline Beecham Corp Derivados sustituidos de tetrahidrofurano-3-onas, de tetrahidropirano-3- onas y tetrahidrotiofen-3-onas, un procedimiento para su preparacion unacomposicion farmaceutica de un medicamento util como inhibidores de proteasas e intermediarios
CN1255119A (zh) * 1997-05-08 2000-05-31 史密丝克莱恩比彻姆公司 蛋白酶抑制剂
EP1062210B1 (en) 1998-03-09 2005-06-01 Vertex Pharmaceuticals Incorporated 1,2-diazepane derivatives as interleukin-1beta converting enzyme inhibitors
EP2261235A3 (en) 1998-03-19 2011-04-20 Vertex Pharmaceuticals Incorporated Inhibitors of caspases
US20030144175A1 (en) 1998-12-23 2003-07-31 Smithkline Beecham Corporation Protease inhibitors
AU765462B2 (en) * 1999-03-16 2003-09-18 Merck Frosst Canada & Co. Gamma-ketoacid dipeptides as inhibitors of caspase-3
AU1588901A (en) 1999-11-10 2001-06-06 Smithkline Beecham Corporation Protease inhibitors
WO2001034600A1 (en) 1999-11-10 2001-05-17 Smithkline Beecham Corporation Protease inhibitors
EP1229914A4 (en) 1999-11-10 2004-06-23 Smithkline Beecham Corp PROTEASE INHIBITORS
AU2001243441B2 (en) 2000-03-21 2004-11-25 Smithkline Beecham Corporation Protease inhibitors
PE20011350A1 (es) 2000-05-19 2002-01-15 Vertex Pharma PROFARMACO DE UN INHIBIDOR DE ENZIMA CONVERTIDORA DE INTERLEUCINA-1ß (ICE)
EP1315971A2 (en) * 2000-07-31 2003-06-04 The Regents of The University of California Model for alzheimer's disease and other neurodegenerative diseases
AU2001293533A1 (en) 2000-09-08 2002-03-22 Merck Frosst Canada & Co. Gamma-ketoacid dipeptides as inhibitors of caspase-3
DE10150203A1 (de) * 2001-10-12 2003-04-17 Probiodrug Ag Peptidylketone als Inhibitoren der DPIV
US7282512B2 (en) 2002-01-17 2007-10-16 Smithkline Beecham Corporation Cycloalkyl ketoamides derivatives useful as cathepsin K inhibitors
CN1980658A (zh) 2004-05-27 2007-06-13 沃泰克斯药物股份有限公司 治疗自身炎性疾病的ice抑制剂
WO2008045017A2 (en) * 2005-06-22 2008-04-17 Diamond Scott L Sars and ebola inhibitors and use thereof, and methods for their discovery
MX359766B (es) 2011-10-14 2018-10-10 Bristol Myers Squibb Co Compuestos de tetrahidroisoquinolina sustituidos como inhibidores del factor xia.
CN103987697B (zh) 2011-10-14 2017-04-26 百时美施贵宝公司 作为因子xia抑制剂的取代的四氢异喹啉化合物
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EP2906552B1 (en) 2012-10-12 2017-11-22 Bristol-Myers Squibb Company Guanidine substituted tetrahydroisoquinoline compounds as factor xia inhibitors
US9403774B2 (en) 2012-10-12 2016-08-02 Bristol-Myers Squibb Company Guanidine and amine substituted tetrahydroisoquinoline compounds as factor xia inhibitors
EP2906551B1 (en) 2012-10-12 2018-02-28 Bristol-Myers Squibb Company Crystalline forms of a factor xia inhibitor
JP6479763B2 (ja) 2013-03-25 2019-03-06 ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ 第ｘｉａ因子阻害剤としての置換アゾール含有のテトラヒドロイソキノリン
NO2760821T3 (es) 2014-01-31 2018-03-10
HRP20181339T1 (hr) 2014-01-31 2018-12-28 Bristol-Myers Squibb Company Makrociklusi sa heterocikličkim p2' grupama kao inhibitori faktora xia
DK3160513T3 (da) 2014-06-30 2020-04-06 Glykos Finland Oy Saccharidderivat af en toksisk payload og antistofkonjugater deraf
CN107074821B (zh) 2014-09-04 2020-05-22 百时美施贵宝公司 为fxia抑制剂的二酰胺大环化合物
US9453018B2 (en) 2014-10-01 2016-09-27 Bristol-Myers Squibb Company Pyrimidinones as factor XIa inhibitors
PH12022553378A1 (en) 2020-06-10 2024-03-25 Univ Leuven Kath Anti-viral compounds for treating coronavirus, picornavirus, and norovirus infections
KR20240035513A (ko) 2021-07-09 2024-03-15 알리고스 테라퓨틱스 인코포레이티드 항바이러스 화합물
WO2023043816A1 (en) 2021-09-17 2023-03-23 Aligos Therapeutics, Inc. Anti-viral compounds for treating coronavirus, picornavirus, and norovirus infections
WO2024018245A1 (en) 2022-07-22 2024-01-25 INSERM (Institut National de la Santé et de la Recherche Médicale) Use of calpain inhibitors for the treatment of the diabetic kidney disease
WO2024153744A1 (en) 2023-01-20 2024-07-25 Institut National de la Santé et de la Recherche Médicale Autophagy activators for the treatment of rhabdomyolysis

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE294176C (es) *
US5055451A (en) * 1986-12-22 1991-10-08 Syntex Inc. Aryloxy and arylacyloxy methyl ketones as thiol protease inhibitors
US5223486A (en) 1988-11-01 1993-06-29 University Research Corporation Inhibition of cancer procoagulant
US4997950A (en) 1989-04-20 1991-03-05 Richard Finbar Murphy Novel C-terminal gastrin antagonists
DD294176A5 (de) * 1990-05-11 1991-09-26 Martin-Luther-Universitaet Halle Wittenberg,De Neue inhibitoren zur hemmung der katalytischen aktivitaet von prolinspezifischen und anderen proteolytischen enzymen und verfahren zu ihrer herstellung

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JPH05246968A (ja) 1993-09-24
DE69229151D1 (de) 1999-06-17
KR100228505B1 (ko) 1999-11-01
KR930002335A (ko) 1993-02-23
DK0525420T3 (da) 1999-11-01
US5639783A (en) 1997-06-17
JP3190431B2 (ja) 2001-07-23
GR3030837T3 (en) 1999-11-30
US5834508A (en) 1998-11-10
DE69229151T2 (de) 1999-11-25
EP0525420A1 (en) 1993-02-03
CA2072834A1 (en) 1993-01-02
ATE179974T1 (de) 1999-05-15
TW239144B (es) 1995-01-21
EP0525420B1 (en) 1999-05-12

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