CO4950618A1 - PROTEASE INHIBITORS - Google Patents

PROTEASE INHIBITORS

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Publication number
CO4950618A1
CO4950618A1 CO98024945A CO98024945A CO4950618A1 CO 4950618 A1 CO4950618 A1 CO 4950618A1 CO 98024945 A CO98024945 A CO 98024945A CO 98024945 A CO98024945 A CO 98024945A CO 4950618 A1 CO4950618 A1 CO 4950618A1
Authority
CO
Colombia
Prior art keywords
alkyl
het
alkenyl
formula
compound
Prior art date
Application number
CO98024945A
Other languages
Spanish (es)
Inventor
Andrew D Gribble
Jason Witherington
Edward Fenwick Ashley
Robert W Marquis
Original Assignee
Smithkline Beecham Corp
Smithkline Beecham Plc
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 Smithkline Beecham Corp, Smithkline Beecham Plc filed Critical Smithkline Beecham Corp
Publication of CO4950618A1 publication Critical patent/CO4950618A1/en

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/99—Enzyme inactivation by chemical treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
    • C07D307/32—Oxygen atoms
    • 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
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • 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
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/06—Anabolic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
    • C07D307/22—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
    • C07D307/83—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, 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
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic 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
    • C07D405/02—Heterocyclic 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
    • C07D405/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Physical Education & Sports Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Immunology (AREA)
  • Microbiology (AREA)
  • Neurology (AREA)
  • Endocrinology (AREA)
  • Biomedical Technology (AREA)
  • General Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Un compuesto según la fórmula (I):en la que:R1 es R", R"C(O), R"C(S), R"SO2 , R"OC(O), R"R´NC(O), o R"OC(O)NR´CH(R6 )C(O);R2 es H, alquilo C1 -C6 , alquenilo C2 -C6 , Ar-alquilo C0 -C6 , o Het-alquilo C0 -C6 ; R3 es H, alquilo C1 -C6 , alquenilo C2 -C6 , alquinilo C2 -C6 , cicloalquil C3 -C6 -alquilo C0 -C6 , Ar-alquilo C0 -C6 , o Het-alquilo C0 -C6 ;R4 es H, alquilo C1 -C6 , alquenilo C2 -C6 , Ar-alquilo C0 -C6 , o Het-alquilo C0 -C6 ;R5 , en cada caso, es independientemente H, alquilo C1 -C6 , alquenilo C2 -C6 , Ar-alquilo C0 -C6 , o Het-alquilo C0 -C6 ;R6 es H, alquilo C1 -C6 , alquenilo C2 -C6 , cicloalquil C3 -C6 -alquilo C0 -C6 , Ar-alquilo C0 -C6 o Het-alquilo C0 -C6 ;R´ es H, alquilo C1 -C6 , alquenilo C2 -C6 , Ar-alquilo C0 -C6 , o Het-alquilo C0 -C6 ;R" es alquilo C1 -C6 , Ar-alquilo C0 -C6 , Het-alquilo C0 -C6 , Ar-alquenilo C2 -C6 , o Het-alquenilo C2 -C6 ;X es O o S; yn es 1, 2 ó 3;o una de sus sales farmacéuticamente aceptables.3Un procedimiento para preparar un compuesto defórmula (I) según la reivindicación 1, procedimiento que comprende:(i) hacer reaccionar un compuesto de fórmula (III): - 2 -en la que R1 , R2 , R3 , R4 , R5 y n son como se definen para la fórmula (I) de la reivindicación 1, con todos sus grupos funcionales reactivos protegidos, con un agente oxidante; o(ii) descarboxilar un compuesto de fórmula (IV):en la que R1 , R2 , R3 , R4 , R5 y n son como se definen para la fórmula (I) de la reivindicación 1, con todos sus grupos funcionales reactivos protegidos; o(iii) hacer reaccionar un compuesto de fórmula (V):en la que R1 , R3 , R4 , R5 y n son como se definen para la fórmula (I) de la reivindicación 1, con todos sus grupos funcionales reactivos protegidos, con un ácido;y, después de ello, eliminar cualquier grupo protector y opcionalmente formar una sal farmacéuticamente aceptable.A compound according to formula (I): in which: R1 is R ", R" C (O), R "C (S), R" SO2, R "OC (O), R" R´NC (O ), or R "OC (O) NR´CH (R6) C (O); R2 is H, C1-C6 alkyl, C2-C6 alkenyl, Ar-C0-C6 alkyl, or Het-C0-C6 alkyl; R3 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl-C0-C6 alkyl, Ar-C0-C6 alkyl, or Het-C0-C6 alkyl; R4 is H, C1 - alkyl C6, C2-C6 alkenyl, Ar-C0 -C6 alkyl, or Het-C0 -C6 alkyl; R5, in each case, is independently H, C1-C6 alkyl, C2-C6 alkenyl, Ar-C0 -C6 alkyl, or Het-C0-C6-alkyl; R6 is H, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl-C0-C6-alkyl, Ar-C0-C6-alkyl or Het-C0 -C6-alkyl; R 'is H, C1-C6-alkyl, C2-C6-alkenyl, Ar-C0-C6-alkyl, or Het-C0-C6-alkyl; R "is C1-C6-alkyl, Ar-C0-C6-alkyl, Het-C0-C6-alkyl, Ar-alkenyl C2-C6, or C2-C6 Het-alkenyl, X is O or S; and n is 1, 2 or 3; or one of its pharmaceutically acceptable salts. 3 A process for preparing a compound of formula (I) according to claim 1, a process comprising: (i) reacting a compound of formula (III): - 2 -wherein R1, R2, R3, R4, R5 and n are as defined for the formula (I) of claim 1, with all its reactive functional groups protected, with an oxidizing agent; or (ii) decarboxylate a compound of formula (IV): wherein R1, R2, R3, R4, R5 and n are as defined for formula (I) of claim 1, with all of their protected reactive functional groups; or (iii) reacting a compound of formula (V): wherein R1, R3, R4, R5 and n are as defined for formula (I) of claim 1, with all of their protected reactive functional groups, with a acid, and thereafter remove any protecting groups and optionally form a pharmaceutically acceptable salt.

CO98024945A 1997-05-06 1998-05-06 PROTEASE INHIBITORS CO4950618A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US4575897P 1997-05-06 1997-05-06

Publications (1)

Publication Number Publication Date
CO4950618A1 true CO4950618A1 (en) 2000-09-01

Family

ID=21939723

Family Applications (1)

Application Number Title Priority Date Filing Date
CO98024945A CO4950618A1 (en) 1997-05-06 1998-05-06 PROTEASE INHIBITORS

Country Status (19)

Country Link
EP (1) EP1003846A4 (en)
JP (1) JP2001525804A (en)
KR (1) KR20010012256A (en)
CN (1) CN1255161A (en)
AR (1) AR013079A1 (en)
AU (1) AU7562598A (en)
BR (1) BR9809306A (en)
CA (1) CA2288868A1 (en)
CO (1) CO4950618A1 (en)
HU (1) HUP0002247A3 (en)
IL (1) IL132088A0 (en)
NO (1) NO995434D0 (en)
NZ (1) NZ337889A (en)
PE (1) PE71599A1 (en)
PL (1) PL336856A1 (en)
TR (1) TR199902766T2 (en)
UY (1) UY25143A1 (en)
WO (1) WO1998050533A1 (en)
ZA (1) ZA983762B (en)

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CO5150165A1 (en) * 1998-11-13 2002-04-29 Smithkline Beecham Plc PROTEASE INHIBITORS: KATEPSIN K TYPE
DZ3083A1 (en) * 1999-02-19 2004-06-02 Smithkline Beecham Corp New protease inhibitor compounds, process for their preparation and pharmaceutical compositions containing them
GB9911417D0 (en) * 1999-05-18 1999-07-14 Peptide Therapeutics Ltd Furanone derivatives as inhibitors of cathepsin s
WO2001034599A1 (en) * 1999-11-10 2001-05-17 Smithkline Beecham Corporation Protease inhibitors
US20040024000A1 (en) * 2000-10-19 2004-02-05 Rajeshwar Singh Dihydropyrimidine derivatives as cysteine protease inhibitors
JP2004513942A (en) * 2000-11-17 2004-05-13 メディヴァー　ユーケイ　リミテッド Cysteine protease inhibitor
JP2004520439A (en) * 2000-11-17 2004-07-08 メディヴィル・アクチボラグ Cysteine protease inhibitor
JP2004522738A (en) * 2001-01-17 2004-07-29 アミュラ テラピューティクス リミテッド Cyclic 2-carbonylaminoketones as inhibitors of cruzipaine and other cysteine proteases
US7132449B2 (en) 2001-01-17 2006-11-07 Amura Therapeutics Limited Inhibitors of cruzipain and other cysteine proteases
AU2002219397B2 (en) * 2001-01-17 2008-02-14 Grünenthal GmbH Inhibitors of cruzipain and other cysteine proteases
NZ526912A (en) * 2001-01-17 2005-02-25 Amura Therapeutics Ltd Inhibitors of cruzipain and other cysteine proteases
WO2003037892A1 (en) * 2001-10-29 2003-05-08 Boehringer Ingelheim Pharmaceuticals, Inc. Compounds useful as reversible inhibitors of cysteine proteases
NZ537853A (en) * 2002-07-16 2007-02-23 Amura Therapeutics Ltd Inhibitors of cathepsin K and related cysteine protesases of the CA clan
KR100962972B1 (en) 2002-07-26 2010-06-09 주식회사유한양행 1-phenylpiperidin-3-one derivatives and processes for the preparation thereof
BRPI0413324A (en) 2003-08-06 2006-10-10 Senomyx Inc t1r hetero-oligomeric taste receptors, cell lines expressing said receptors, and taste compounds
AU2016206281B2 (en) * 2003-08-06 2017-11-30 Senomyx, Inc. Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
DE602005019971D1 (en) * 2004-01-08 2010-04-29 Medivir Ab INHIBITORS OF CYSTONE PROTEASE
CA2619706A1 (en) * 2005-08-17 2007-02-22 Schering Corporation Novel high affinity quinoline-based kinase ligands
GB0614042D0 (en) 2006-07-14 2006-08-23 Amura Therapeutics Ltd Compounds
MX2009012847A (en) * 2007-06-13 2009-12-08 Bristol Myers Squibb Co Dipeptide analogs as coagulation factor inhibitors.
US7893067B2 (en) 2007-06-27 2011-02-22 Medivir Ab Cysteine protease inhibitors
EP2240491B1 (en) 2008-01-09 2015-07-15 Amura Therapeutics Limited TETRAHYDROFURO(2,3-b)PYRROL-3-ONE DERIVATIVES AS INHIBITORS OF CYSTEINE PROTEINASES
GB0817424D0 (en) * 2008-09-24 2008-10-29 Medivir Ab Protease inhibitors

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JPH05140063A (en) * 1991-11-19 1993-06-08 Suntory Ltd Dipeptide derivative and medicine for preventing and improving osteopathy, containing the same compound as active component
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JP2848232B2 (en) * 1993-02-19 1999-01-20 武田薬品工業株式会社 Aldehyde derivatives
JP3599287B2 (en) * 1993-04-28 2004-12-08 三菱化学株式会社 Sulfonamide derivative
US5403952A (en) * 1993-10-08 1995-04-04 Merck & Co., Inc. Substituted cyclic derivatives as novel antidegenerative agents
SK88997A3 (en) * 1995-10-30 1998-05-06 Smithkline Beecham Corp Method of inhibiting cathepsin k
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WO1998004539A1 (en) * 1996-07-29 1998-02-05 Mitsubishi Chemical Corporation Oxygenic heterocyclic derivatives

Also Published As

Publication number Publication date
NO995434L (en) 1999-11-05
KR20010012256A (en) 2001-02-15
TR199902766T2 (en) 2000-02-21
CA2288868A1 (en) 1998-11-12
EP1003846A1 (en) 2000-05-31
WO1998050533A1 (en) 1998-11-12
NO995434D0 (en) 1999-11-05
PL336856A1 (en) 2000-07-17
UY25143A1 (en) 1998-11-27
JP2001525804A (en) 2001-12-11
IL132088A0 (en) 2001-03-19
AR013079A1 (en) 2000-12-13
AU7562598A (en) 1998-11-27
CN1255161A (en) 2000-05-31
HUP0002247A3 (en) 2003-01-28
PE71599A1 (en) 1999-09-15
HUP0002247A2 (en) 2001-05-28
BR9809306A (en) 2000-07-04
EP1003846A4 (en) 2002-11-13
NZ337889A (en) 2001-09-28
ZA983762B (en) 1998-11-06

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