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PE20080906A1 - HETEROARYL DERIVATIVES AS CYTOKINE INHIBITORS - Google Patents

HETEROARYL DERIVATIVES AS CYTOKINE INHIBITORS

Info

Publication number
PE20080906A1
PE20080906A1 PE2007001096A PE2007001096A PE20080906A1 PE 20080906 A1 PE20080906 A1 PE 20080906A1 PE 2007001096 A PE2007001096 A PE 2007001096A PE 2007001096 A PE2007001096 A PE 2007001096A PE 20080906 A1 PE20080906 A1 PE 20080906A1
Authority
PE
Peru
Prior art keywords
alkyl
ter
aryl
phenyl
butyl
Prior art date
Application number
PE2007001096A
Other languages
Spanish (es)
Inventor
Erik Boman
Justin Ernst
Montalban Antonio Garrido
Christopher J Larson
Christopher Lum
Yazhong Pei
Lubomir Sebo
Jan Urban
Zhijun Wang
Jay Zhu
Original Assignee
Kemia Inc
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 Kemia Inc filed Critical Kemia Inc
Publication of PE20080906A1 publication Critical patent/PE20080906A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic 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
    • C07D295/04—Heterocyclic 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
    • C07D295/12—Heterocyclic 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
    • C07D295/135—Heterocyclic 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
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D413/10—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 carbon chain containing aromatic rings
    • 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
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/18—Bridged systems

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

REFERIDA A UN COMPUESTO HETEROARILO DE FORMULA (I), DONDE X ES CH, N O NO; Y ES CH, N, NO, CON LA CONDICION DE QUE X E Y NO SEAN AMBOS CH O NO; A ES F, Cl, NR2, ALQUILO C1-C3, ENTRE OTROS; G ES UN GRUPO ARILO O HETEROARILO, DONDE G SE SUSTITUYE POR UNO OMAS R1, R2 O R3; Ar ES UN GRUPO ARILO O HETEROARILO DE 6 MIEMBROS; L1 ES C(O)NH; L2 ES UN ENLACE COVALENTE, (CR'2)s, (CR'2)nO(CR'2)t, ENTRE OTROS; Q ES ALQUILO, CICLOALQUILO, ARILO, ENTRE OTROS; R1 ES F, Cl, NR2, CN, ENTRE OTROS; R2 ES Cl, CN, NO2, OR, ENTRE OTROS; R3 ES ALQUILO, ALQUENILO, ALQUINILO, ENTRE OTROS; R ES H, ALQUILO C1-C6, ENTRE OTROS; R' ES H, ALQUILO, CICLOALQUILO, ENTRE OTROS; n ES 0, 1 O 2; s ES 1, 2 O3; t ES 0, 1 O 2; CON LA CONDICION DE QUE EL COMPUESTO NO SEA 5-(BIFENIL-4-IL)-6-CLORO-N-(6-METOXIPIRIDIN-3-IL)NICOTINAMIDA. SON COMPUESTOS PREFERIDOS: 3-TER-BUTIL-5-CIANO-N-(6-METIL-5-(3-(NEOPENTILCARBAMOIL)FENIL)-PIRIDIN-3-IL)BENZAMIDA, N-(5-(4-(BENCILOXI)FENIL)-6-METILPIRIDIN-3-IL)-3-TER-BUTIL-5-CIANOBENZAMIDA, 3-TER-BUTIL-5-CIANO-N-(5-(4-(3,3-DIMETIL-2-OXOBUTOXI)FENIL)-6-METILPIRIDIN-3-IL)BENZAMIDA, ENTRE OTROS. TAMBIEN ESTA REFERIDA A UNA COMPOSICION FARMACEUTICA Y A UN PROCEDIMIENTO DE PREPARACIUON. DICHOS COMPUESTOS SON INHIBIDORES DE CITOCINA Y SON UTILES EN EL TRATAMIENTO DE ENFERMEDADES AUTOINMUNES, INFLAMATORIAS, CANCER, ENTRE OTRASREFERRING TO A HETEROARYL COMPOUND OF FORMULA (I), WHERE X IS CH, N OR NO; Y IS CH, N, NO, WITH THE CONDITION THAT X AND Y ARE NOT BOTH CH OR NOT; A IS F, Cl, NR2, C1-C3 ALKYL, AMONG OTHERS; G IS AN ARYL OR HETEROARYL GROUP, WHERE G IS REPLACED BY ONE OMAS R1, R2 OR R3; Ar IS AN ARYL OR HETEROARY GROUP OF 6 MEMBERS; L1 IS C (O) NH; L2 IS A COVALENT LINK, (CR'2) s, (CR'2) nO (CR'2) t, AMONG OTHERS; Q IS ALKYL, CYCLOALKYL, ARYL, AMONG OTHERS; R1 IS F, Cl, NR2, CN, AMONG OTHERS; R2 IS Cl, CN, NO2, OR, AMONG OTHERS; R3 IS RENTAL, ALKENYL, ALKINYL, AMONG OTHERS; R IS H, C1-C6 ALKYL, AMONG OTHERS; R 'IS H, ALKYL, CYCLOALKYL, AMONG OTHERS; n IS 0, 1 O 2; s IS 1,2 O3; t IS 0, 1 O 2; WITH THE CONDITION THAT THE COMPOUND IS NOT 5- (BIPHENYL-4-IL) -6-CHLORO-N- (6-METOXIPIRIDIN-3-IL) NICOTINAMIDE. PREFERRED COMPOUNDS ARE: 3-TER-BUTYL-5-CYAN-N- (6-METHYL-5- (3- (NEOPENTILCARBAMOIL) PHENYL) -PYRIDIN-3-IL) BENZAMIDE, N- (5- (4- (BENZYLOXY ) PHENYL) -6-METHYLPYRIDIN-3-IL) -3-TER-BUTYL-5-CYANOBENZAMIDE, 3-TER-BUTYL-5-CYANE-N- (5- (4- (3,3-DIMETHYL-2- OXOBUTOXI) PHENYL) -6-METHYLPYRIDIN-3-IL) BENZAMIDE, AMONG OTHERS. IT ALSO REFERS TO A PHARMACEUTICAL COMPOSITION AND A PREPARATION PROCEDURE. SUCH COMPOUNDS ARE INHIBITORS OF CYTOKINE AND ARE USEFUL IN THE TREATMENT OF AUTOIMMUNE, INFLAMMATORY, CANCER, AMONG OTHERS

PE2007001096A 2006-08-17 2007-08-15 HETEROARYL DERIVATIVES AS CYTOKINE INHIBITORS PE20080906A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83879506P 2006-08-17 2006-08-17
US89147007P 2007-02-23 2007-02-23

Publications (1)

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PE20080906A1 true PE20080906A1 (en) 2008-07-05

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Family Applications (1)

Application Number Title Priority Date Filing Date
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Country Status (5)

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AR (1) AR062427A1 (en)
CL (1) CL2007002375A1 (en)
PE (1) PE20080906A1 (en)
TW (1) TW200815422A (en)
WO (1) WO2008021388A1 (en)

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