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UY25143A1 - PROCEDURE FOR THE PREPARATION OF PROTEASE INHIBITORS. - Google Patents

PROCEDURE FOR THE PREPARATION OF PROTEASE INHIBITORS.

Info

Publication number
UY25143A1
UY25143A1 UY25143A UY25143A UY25143A1 UY 25143 A1 UY25143 A1 UY 25143A1 UY 25143 A UY25143 A UY 25143A UY 25143 A UY25143 A UY 25143A UY 25143 A1 UY25143 A1 UY 25143A1
Authority
UY
Uruguay
Prior art keywords
alkyl
het
alkenyl
cysteine proteases
inhibitors
Prior art date
Application number
UY25143A
Other languages
Spanish (es)
Inventor
F Veber Daniel
D Gribble Andrew
Witherington J
E Fenwick Ashley
Robert Marquis
Original Assignee
Smithkline Beecham Corp Y Smithkline Beecham P L C
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 Y Smithkline Beecham P L C filed Critical Smithkline Beecham Corp Y Smithkline Beecham P L C
Publication of UY25143A1 publication Critical patent/UY25143A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26Heterocyclic 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
    • C07D307/30Heterocyclic 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
    • C07D307/32Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/99Enzyme inactivation by chemical treatment
    • 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
    • A61P1/02Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/08Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • A61P21/06Anabolic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04Heterocyclic 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
    • C07D307/18Heterocyclic 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
    • C07D307/22Nitrogen atoms not forming part of a nitro radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic 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
    • C07D307/78Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82Benzo [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
    • C07D307/83Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic 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
    • C07D307/78Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/86Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16Heterocyclic 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
    • C07D309/28Heterocyclic 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
    • C07D309/30Oxygen atoms, e.g. delta-lactones
    • 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
    • C07D407/00Heterocyclic 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
    • C07D407/02Heterocyclic 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
    • C07D407/12Heterocyclic 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
    • 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
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12Heterocyclic 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)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Biomedical Technology (AREA)
  • Endocrinology (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Immunology (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Neurology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyrane Compounds (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Procedimiento para preparar compuestos derivados n-sustituidos de 4-amino-tetrahidrofuran-3-ona, 4-aminotetrahidropiran-3-ona y 4-aminotetrahidrotiofen-3-ona utilizados como inhibidores de cisteína proteasas, particularmente catepsina k. Son útiles en el tratamiento de enfermedades caracterizadas por la pérdida excesiva de hueso o cartílago, por ejemplo osteoporosis, periodontitis y artritis, en las que están implicadas cisteína proteasas. Es un compuesto de fórmula l en que: R1 es R'', R''C(O), R''C(S), R''OC(O), CH(R6)C(O); R2 es H, alquilo, alquenilo, Ar-alquilo, o Het-alquilo; R3 es H, alquilo, alquenilo, alquinilo, cicloalquil, Het-alquilo; R4 es H, alquilo, alquenilo, Ar-alquilo, Het-alquilo; R5 en cada caso, es independientemente H, alquilo, alquenilo, Ar-alquilo, Het-alquilo; X es O o S; y nes 1,2 o 3; o una sal farmacéuticamente aceptables, que son inhibidores de cisteína proteasas. Ejemplo de un compuesto de fórmula l sería: 4-(R, S)-Amino-N-[(3,4-diclorobenzoil)-S-leucina]-tetrahidrofuran-3-ona.Process for preparing n-substituted derivative compounds of 4-amino-tetrahydrofuran-3-one, 4-aminotetrahydropyran-3-one and 4-aminotetrahydrothiophen-3-one used as inhibitors of cysteine proteases, particularly cathepsin k. They are useful in the treatment of diseases characterized by excessive loss of bone or cartilage, for example osteoporosis, periodontitis and arthritis, in which cysteine proteases are involved. It is a compound of formula I in which: R1 is R ", R" C (O), R "C (S), R" OC (O), CH (R6) C (O); R2 is H, alkyl, alkenyl, Ar-alkyl, or Het-alkyl; R3 is H, alkyl, alkenyl, alkynyl, cycloalkyl, Het-alkyl; R4 is H, alkyl, alkenyl, Ar-alkyl, Het-alkyl; R5 at each occurrence is independently H, alkyl, alkenyl, Ar-alkyl, Het-alkyl; X is O or S; and nes 1,2 or 3; or a pharmaceutically acceptable salt, which are inhibitors of cysteine proteases. Example of a compound of formula I would be: 4- (R, S) -Amino-N - [(3,4-dichlorobenzoyl) -S-leucine] -tetrahydrofuran-3-one.

UY25143A 1997-05-06 1998-08-17 PROCEDURE FOR THE PREPARATION OF PROTEASE INHIBITORS. UY25143A1 (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
UY25143A1 true UY25143A1 (en) 1998-11-27

Family

ID=21939723

Family Applications (1)

Application Number Title Priority Date Filing Date
UY25143A UY25143A1 (en) 1997-05-06 1998-08-17 PROCEDURE FOR THE PREPARATION OF 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) NO995434L (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)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
AU1588901A (en) * 1999-11-10 2001-06-06 Smithkline Beecham Corporation Protease inhibitors
US20040024000A1 (en) * 2000-10-19 2004-02-05 Rajeshwar Singh Dihydropyrimidine derivatives as cysteine protease inhibitors
EP1345931A2 (en) * 2000-11-17 2003-09-24 Medivir UK Ltd Cysteine protease inhibitors
WO2002088106A2 (en) * 2000-11-17 2002-11-07 Medivir Ab Cysteine protease inhibitors
US6958358B2 (en) 2001-01-17 2005-10-25 Amura Therapeutics Limited Inhibitors of cruzipain and other cysteine proteases
CN1269822C (en) * 2001-01-17 2006-08-16 阿姆拉医疗有限公司 Inhibitors of Cruz protease and other cysteine proteases
CA2435117A1 (en) * 2001-01-17 2002-07-25 Amura Therapeutics Limited Cyclic 2-carbonylaminoketones as inhibitors of cruzipain and other cysteine proteases
US7132449B2 (en) 2001-01-17 2006-11-07 Amura Therapeutics Limited 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
WO2004007501A1 (en) * 2002-07-16 2004-01-22 Amura Therapeutics Limited Biologically active compounds
KR100962972B1 (en) 2002-07-26 2010-06-09 주식회사유한양행 1-phenylpiperidin-3-one derivatives and preparation method thereof
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
CA2535045A1 (en) 2003-08-06 2005-02-17 Senomyx, Inc. T1r hetero-oligomeric taste receptors, cell lines that express said receptors, and taste compounds
EP1701960B1 (en) * 2004-01-08 2010-03-17 Medivir Aktiebolag Cysteine protease inhibitors
WO2007022241A2 (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
WO2009087379A2 (en) 2008-01-09 2009-07-16 Amura Therapeutics Limited Tetrahydrofuro (3, 2 -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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JP3190431B2 (en) * 1991-07-01 2001-07-23 三菱化学株式会社 Ketone derivatives
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
CA2111930A1 (en) * 1992-12-25 1994-06-26 Ryoichi Ando Aminoketone derivatives
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
TW448172B (en) * 1996-03-08 2001-08-01 Pharmacia & Upjohn Co Llc Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation
WO1998004539A1 (en) * 1996-07-29 1998-02-05 Mitsubishi Chemical Corporation Oxygenic heterocyclic derivatives

Also Published As

Publication number Publication date
EP1003846A1 (en) 2000-05-31
EP1003846A4 (en) 2002-11-13
NZ337889A (en) 2001-09-28
CA2288868A1 (en) 1998-11-12
AR013079A1 (en) 2000-12-13
CO4950618A1 (en) 2000-09-01
PL336856A1 (en) 2000-07-17
TR199902766T2 (en) 2000-02-21
WO1998050533A1 (en) 1998-11-12
IL132088A0 (en) 2001-03-19
HUP0002247A2 (en) 2001-05-28
CN1255161A (en) 2000-05-31
JP2001525804A (en) 2001-12-11
AU7562598A (en) 1998-11-27
KR20010012256A (en) 2001-02-15
HUP0002247A3 (en) 2003-01-28
BR9809306A (en) 2000-07-04
ZA983762B (en) 1998-11-06
NO995434D0 (en) 1999-11-05
NO995434L (en) 1999-11-05
PE71599A1 (en) 1999-09-15

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Effective date: 20001213