AR050858A1 - COMPOSITE HETEROARIL-NITRILO REPLACED, ITS USE FOR THE MANUFACTURE OF A MEDICINAL PRODUCT, PHARMACEUTICAL COMPOSITION THAT INCLUDES IT AND PROCEDURE FOR THE PREPARATION OF THE SAME - Google Patents

COMPOSITE HETEROARIL-NITRILO REPLACED, ITS USE FOR THE MANUFACTURE OF A MEDICINAL PRODUCT, PHARMACEUTICAL COMPOSITION THAT INCLUDES IT AND PROCEDURE FOR THE PREPARATION OF THE SAME

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Publication number
AR050858A1
AR050858A1 ARP050103711A ARP050103711A AR050858A1 AR 050858 A1 AR050858 A1 AR 050858A1 AR P050103711 A ARP050103711 A AR P050103711A AR P050103711 A ARP050103711 A AR P050103711A AR 050858 A1 AR050858 A1 AR 050858A1
Authority
AR
Argentina
Prior art keywords
alkyl
aryl
heteroaryl
heterocyclyl
alkylene
Prior art date
Application number
ARP050103711A
Other languages
Spanish (es)
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Glaxo Group Ltd
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Publication date
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Publication of AR050858A1 publication Critical patent/AR050858A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/12—Heterocyclic 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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic 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
    • C07D413/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Un compuesto de heteroaril-nitrilo sustituido de formula (1): en donde: R1 representa alquilo C1-8, -alquilen C1-8-NRERF, -alquilen C1-8-NRGC(O)O-alquilo C1-6, -alquilen C1-8NRGC(O)-alquilo C1-6 o -alquilen C1-8-cicloalquilo; R3 representa H o alquilo C1-6; R4 representa H o alquilo C1-6; y a) X representa NR5 y A representa C(O) y i) R2 representa R2a en donde R2a representa -NRH-arilo, -NRH-heteroarilo, -NRH-aril-heteroarilo o -NRH-heteroaril-arilo; y R2b representa -alquilen C1-6-RA, arilo, biarilo, -aril-heteroarilo, -heteroaril-arilo, -aril-heterociclilo, -aril-alquilen C1-3-heterociclilo, -aril-O-alquilen C1-3-heterociclilo, aril-alquilen C1-3-heteroarilo, -aril-heteroaril-alquilen C1-3-heterociclilo, -heteroaril-aril- alquilen C1-3-heterociclilo, ariloxi, heteroarilo, cicloalquilo, -cicloalquil-arilo, cicloalquiloxi, heterociclilo, -NRH-aril-heterociclilo, -NRH-cicloalquilo, -NRB-alquilen C1-6-RC, -O-alquilen C1-6RD o -O-alquenilo C1-6; -aril-alquilen C1-3- heterociclil-RJ, -aril-alquilen C1-3-heteroaril-RK, alquilen C1-3(NH2)-arilo; y R5 representa H, alquilo C1-6, alquenilo C1-6, -C(O)R2a, -alquilen C1-8-heterociclilo, -alquilen C1-8-NRGC(O)-alquilo C1-6, -alquilen C1-8NRGC(O)O-alquilo C1-6, - alquilen C1-8NRERF, N-ftalidimido-alquilen C1-8- o -C(O)-alquilo C1-6; o ii) R2 y R5 junto con los átomos de C y N a los que están respectivamente unidos forman un grupo seleccionado de los restos de formulas (2), o b) X representa NR5 y A representa -SO2- y R2 representa alquilo C1-6 o aralquilo C1-6; y R5 representa H, alquilo C1-6, alquenilo C1-6, -alquilen C1-8-heterociclilo, -alquilen C1-8-NRGC(O)-alquilo C1-6, -alquilen C1-8NRGC(O)O-alquilo C1-6, -alquilen C1-8NRERF, N- ftalidimido-alquilen C1-8- o -C(O)-alquilo C1-6; o c) X representa CH2 y A representa C(O) y R2 representa -NRH-arilo, -NRH-heteroarilo, -NRH-aralquilo C1-6, -NRH-alquilen C1-6-heteroarilo, -NRH-aril-heteroarilo, -NRH-aril-heterociclilo o -O- aralquilo C1-6; en la que RA, RC y RD independientemente representan H, halogeno, -NRERF, ciano, CCl3, -C(O)-alquilo C1-6, alquilo C1-3, cicloalquilo, heterociclilo, arilo, biarilo, -aril-heteroarilo, -aril-alquilen C1-3-heterociclilo, -aril-O- alquilen C1-3-heterociclilo, -alquenil C1-3-arilo, heteroarilo, aralquilo C1-6, -NHC(O)-alquilo C1-6, -NHC(O)O-alquilo C1-6, -NHC(O)-aralquilo C1-6 o -NHC(O)O-aralquilo C1-6; RB representa H o alquilo C1-8; Re y RF independientemente representan H o alquilo C1-3; o RE representa cicloalquilo y RF representa H; o RE y RF junto con el átomo de N al que están unidos forman un anillo heterocíclico de 5 o 6 miembros; RG representa H o alquilo C1-3; RH representa H, alquilo C1-6, -alquilen C1-6- NHC(O)-alquilo C1-4, -alquilen C1-6-NHC(O)O-alquilo C1-4 o -alquilen C1-6-NRERF; RJ representa arilo, heteroarilo, heterociclilo, -alquilen C1-3(arilo)2, -alquilen C1-3-heteroarilo, -aralquilo C1-3, -alquilen C1-3-oxo-heterociclilo, -O-C(O)-alquilen C1-3-arilo; RK representa uno o dos sustituyentes arilo; y sus sales y solvatos. Composicion farmacéutica que comprende dicho compuesto y su uso para la preparacion de dicha composicion util para el tratamiento de afecciones susceptibles de mediacion por un inhibidor de cistaína proteasa, como malaria o enfermedades oseas, de cartílagos o articulaciones. Procedimiento para la preparacion de dicho compuesto.A substituted heteroaryl-nitrile compound of formula (1): wherein: R 1 represents C 1-8 alkyl, -C 1-8-NRERF-alkyl, C 1-8-NRGC (O) O-C 1-6 alkyl, -alkylene C1-8NRGC (O) -C 1-6 alkyl or -C 1-8 alkyl-cycloalkyl; R3 represents H or C1-6 alkyl; R4 represents H or C1-6 alkyl; and a) X represents NR5 and A represents C (O) and i) R2 represents R2a wherein R2a represents -NRH-aryl, -NRH-heteroaryl, -NRH-aryl-heteroaryl or -NRH-heteroaryl-aryl; and R2b represents -C1-6-RA-alkylene, aryl, biaryl, -aryl-heteroaryl, -heteroaryl-aryl, -aryl-heterocyclyl, -aryl-C1-3-heterocyclyl alkylene, -aryl-O-C1-3-alkylene heterocyclyl, aryl-C 1-3 alkaryl-heteroaryl, -aryl-heteroaryl-C 1-3-heterocyclyl, -heteroaryl-aryl-C 1-3-heterocyclyl, aryloxy, heteroaryl, cycloalkyl, -cycloalkyl-aryl, cycloalkyloxy, heterocyclyl, -NRH-aryl-heterocyclyl, -NRH-cycloalkyl, -NRB-C1-6-alkylene, -O-C1-6RD alkylene or -O-C1-6 alkenyl; -aryl-C1-3alkyl-heterocyclyl-RJ, -aryl-C1-3alkyl-heteroaryl-RK, C1-3alkyl (NH2) -aryl; and R5 represents H, C1-6 alkyl, C1-6 alkenyl, -C (O) R2a, -C 1-8 alkyl-heterocyclyl, -C 1-8 alkylene-NRGC (O) -C 1-6 alkyl, -C 1-10 alkylene 8NRGC (O) O-C1-6 alkyl, - C1-8 alkylene-NRERF, N-phthalidimido-C1-8-alkylene or -C (O) -C1-6 alkyl; or ii) R2 and R5 together with the atoms of C and N to which they are respectively attached form a group selected from the moieties of formulas (2), b) X represents NR5 and A represents -SO2- and R2 represents C1- alkyl 6 or C1-6 aralkyl; and R5 represents H, C1-6 alkyl, C1-6 alkenyl, -C1-8-heterocyclyl, -C1-8-NRGC (O) -C1-6 alkyl, -C1-8NRGC (O) O-alkyl C1-6, -C1-8NRERF alkylene, N- phthalimidido-C1-8- or -C (O) -C1-6 alkyl; or c) X represents CH2 and A represents C (O) and R2 represents -NRH-aryl, -NRH-heteroaryl, -NRH-C1-6 aralkyl, -NRH-C1-6-heteroaryl alkylene, -NRH-aryl-heteroaryl, -NRH-aryl-heterocyclyl or -O- C1-6 aralkyl; in which RA, RC and RD independently represent H, halogen, -NRERF, cyano, CCl3, -C (O) -C1-6 alkyl, C1-3 alkyl, cycloalkyl, heterocyclyl, aryl, biaryl, -aryl-heteroaryl, -aryl-C1-3alkyl-heterocyclyl, -aryl-O- C1-3alkyl-heterocyclyl, -C1-3alkyl-aryl, heteroaryl, C1-6alkyl, -NHC (O) -C1-6alkyl, -NHC (O) O-C 1-6 alkyl, -NHC (O) -C 1-6 alkyl or -NHC (O) O-C 1-6 alkyl; RB represents H or C1-8 alkyl; Re and RF independently represent H or C1-3 alkyl; or RE represents cycloalkyl and RF represents H; or RE and RF together with the N atom to which they are attached form a 5- or 6-membered heterocyclic ring; RG represents H or C1-3 alkyl; RH represents H, C 1-6 alkyl, -C 1-6 alkyl-NHC (O) -C 1-4 alkyl, -C 1-6 alkyl-NHC (O) O-C 1-4 alkyl or -C 1-6 alkylene-NRERF; RJ represents aryl, heteroaryl, heterocyclyl, -C1-3alkyl (aryl) 2, -C1-3-heteroaryl, -C1-3alkyl, -C1-3-oxo-heterocyclyl, -OC (O) -C1 alkylene -3-aryl; RK represents one or two aryl substituents; and its salts and solvates. Pharmaceutical composition comprising said compound and its use for the preparation of said composition useful for the treatment of conditions susceptible to mediation by a cystaine protease inhibitor, such as malaria or bone diseases, cartilage or joints. Procedure for the preparation of said compound.

ARP050103711A 2004-09-07 2005-09-05 COMPOSITE HETEROARIL-NITRILO REPLACED, ITS USE FOR THE MANUFACTURE OF A MEDICINAL PRODUCT, PHARMACEUTICAL COMPOSITION THAT INCLUDES IT AND PROCEDURE FOR THE PREPARATION OF THE SAME AR050858A1 (en)

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EP04381032 2004-09-07

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AR050858A1 true AR050858A1 (en) 2006-11-29

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ARP050103711A AR050858A1 (en) 2004-09-07 2005-09-05 COMPOSITE HETEROARIL-NITRILO REPLACED, ITS USE FOR THE MANUFACTURE OF A MEDICINAL PRODUCT, PHARMACEUTICAL COMPOSITION THAT INCLUDES IT AND PROCEDURE FOR THE PREPARATION OF THE SAME

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AR (1) AR050858A1 (en)
PE (1) PE20060718A1 (en)
TW (1) TW200624429A (en)
WO (1) WO2006027211A1 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CL2007001794A1 (en) * 2006-06-20 2008-01-18 Wyeth Corp Compounds derived from 2-imidazolidinone, potassium channel inhibitors kv1.5; pharmaceutical composition that includes them; and its use to treat or prevent cardiac arrhythmias. thromboembolism, stroke, heart failure.
EP2030621A1 (en) * 2007-08-21 2009-03-04 Glaxo Group Limited Novel substituted pyrimidines as cysteine protease inhibitors
EP2077841A1 (en) * 2006-10-30 2009-07-15 Glaxo Group Limited Novel substituted pyrimidines as cysteine protease inhibitors
EP1918284A1 (en) * 2006-10-30 2008-05-07 Glaxo Group Hydrazinopyrimidines as cysteine protease inhibitors
JP2010520254A (en) * 2007-03-02 2010-06-10 グラクソ グループ リミテッド Purines as cysteine protease inhibitors
EP1972630A1 (en) * 2007-03-02 2008-09-24 Glaxo Group Limited Purines as cysteine protease inhibitors
DE102008063561A1 (en) * 2008-12-18 2010-08-19 Bayer Cropscience Ag Hydrazides, process for their preparation and their use as herbicides and insecticides

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Publication number Priority date Publication date Assignee Title
AR036375A1 (en) * 2001-08-30 2004-09-01 Novartis Ag PIRROLO [2,3-D] PIRIMIDINE -2- CARBONITRILE COMPOUNDS, A PROCESS FOR THEIR PREPARATION, A PHARMACEUTICAL COMPOSITION AND THE USE OF SUCH COMPOUNDS FOR THE PREPARATION OF MEDICINES
UY27813A1 (en) * 2002-05-31 2003-12-31 Smithkline Beecham Corp PEPTIDE-DISFORMILASE INHIBITORS
GB0220187D0 (en) * 2002-08-30 2002-10-09 Novartis Ag Organic compounds

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TW200624429A (en) 2006-07-16
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