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WO2002034748A1 - Derives d'imidazopyridine - Google Patents

Derives d'imidazopyridine Download PDF

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Publication number
WO2002034748A1
WO2002034748A1 PCT/JP2001/009258 JP0109258W WO0234748A1 WO 2002034748 A1 WO2002034748 A1 WO 2002034748A1 JP 0109258 W JP0109258 W JP 0109258W WO 0234748 A1 WO0234748 A1 WO 0234748A1
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Prior art keywords
group
carbon atoms
substituted
methyl
compound
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PCT/JP2001/009258
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English (en)
Japanese (ja)
Inventor
Ichiro Hayakawa
Yuichi Sugano
Toshinori Agatsuma
Hidehiko Furukawa
Shinichi Kurakata
Shunji Naruto
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Sankyo Co Ltd
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Sankyo Co Ltd
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Priority to AU2001295992A priority Critical patent/AU2001295992A1/en
Publication of WO2002034748A1 publication Critical patent/WO2002034748A1/fr
Anticipated expiration legal-status Critical
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    • 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
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention relates to a novel imidazopyridine derivative ⁇ having excellent tumor 'growth inhibition activity. Akira
  • the present inventors have conducted extensive studies on the synthesis of a derivative having an excellent tumor growth inhibitory activity and its pharmacological activity over many years, and have found that a novel imidazopyridine derivative has an excellent tumor growth inhibitory activity. Completed the invention.
  • novel imidazopyridine derivative of the present invention is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-oxidethyl
  • R 1 and R 2 are the same or different and each have the formula R g — X 2 — group (wherein, R 9 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, and is selected from ⁇ group below.
  • R 3 , R ⁇ R 5 , R 6 , R 7 and R 8 may be the same or different and are each a halogen atom, a cyano group, an ethoxy group, a formula R 1Q —X 3 group (wherein, R 1C) is hydrogen Atom, alkyl group having 1 to 6 carbon atoms, alkyl group having 1 to 6 carbon atoms substituted with 1 to 3 substituents selected from the following ⁇ group, cycloalkyl group having 3 to 8 members, A 3- to 8-membered cycloalkyl group substituted by 1 to 3 with a substituent selected from Group 3, an aryl group having 6 to 14 carbon atoms, and 1) a substituent selected from Group 3 5 to 5 substituted aralkyl groups having 6 to 14 carbon atoms, heterocyclic groups, heterocyclic groups substituted with 1 to 5 substituents selected from the following / 3 groups, aralkyl having 7 to 15 carbon atoms A) a alkenyl group having 7
  • R 11 and R 12 are the same or different and are a group of the formula R 13 — X 4 , wherein R 13 is a hydrogen atom, a carbon atom number of 1 to 6 alkyl groups, alkyl groups having 1 to 6 carbon atoms, 1 to 6 carbon atoms substituted by 1 to 3 substituents selected from the following ⁇ group, 3 to 8 membered cycloalkyl groups, selected from the following 3 groups A 3- to 8-membered cycloalkyl group substituted with 1 to 3 substituents, an aryl group having 6 to 14 carbon atoms, An aryl group having 6 to 14 carbon atoms, a heterocyclic group substituted by 1 to 5 with a substituent selected from the following ⁇ group, a heterocyclic group substituted by 1 to 5 with a substituent selected from the following group: Ring group, aralkyl group having 7 to 15 carbon atoms, aralkyl group having 7 to 15
  • R 3 , RR 7, and R 8 are the same and represent a benzene ring which may have a substituent together with R 5 and R 6 and the carbon to which each is bonded.
  • R 3 , RR 5 and R 8 have the same meaning, and together with R 6 and R 7 , together with the carbon to which each is attached, represents a benzene ring which may have a substituent;
  • RR 5 and R 6 is a same meaning, indicating a benzene ring which may have a substituent together with the carbon to which respectively R 7 and R 8 are attached.
  • X 1 represents an oxygen atom, a sulfur atom, or a formula NH group.
  • ⁇ group halogen atom, cyano group, ethoxy group, oxodioxorenylmethyl group, formula R 14 — X s group (wherein, “R” is a hydrogen atom, an amino group, a C 1-20 An alkyl group, an alkyl group having 1 to 20 carbon atoms substituted by 1 to 3 substituents selected from the following ⁇ group, a 3 to 8 membered cycloalkyl group, a substituent selected from the following ⁇ group: 1 to 3 substituted 3 to 8 membered cycloalkyl group, 6 to 14 carbon atoms aryl group, 6 to 14 carbon atoms substituted by 1 to 5 substituents selected from the following ⁇ group Aryl group, heterocyclic group, a heterocyclic group substituted by 1 to 3 with a substituent selected from the following group ⁇ , an aralkyl group having 7 to 15 carbon atoms, 1 to 1 a substituent selected from the following group ⁇ 5 substituted
  • R 16 and R 17 together with the bonding nitrogen atom represent a heterocyclic group or a heterocyclic group substituted by 1 to 5 with a substituent selected from the following group ⁇ , provided that the formula R "— X 5 does not represent an alkyl group having 1 to 6 carbon atoms.
  • R 18 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituent selected from the following ⁇ group: 1 to 3 3-substituted alkyl group having 1 to 6 carbon atoms, 3- to 8-membered cycloalkyl group, 3- to 8-membered cycloalkyl group substituted by 1 to 3 with a substituent selected from the following group ⁇
  • a heterocyclic group selected from the following group ⁇ : A heterocyclic group substituted with 1 to 5 carbon atoms, an aralkyl group having 7 to 15 carbon atoms, an aralkyl group having 7 to 15 carbon atoms substituted with 1 to 5 substituents selected from the following ⁇ group
  • R 19 R ⁇ N— group (wherein R 19 and R 2 ° are the same or different, and the formula R 21 — X 8 group (where R 21 is a hydrogen atom, a carbon number) 1 to 6 alkyl groups, an alkyl group having 1 to 6 carbon atoms substituted by 1 to 3 with a substituent selected from the following ⁇ group, a 3 to 8 membered cycloalkyl group, selected from the following ⁇ group: A 3- to 8-membered cycloalkyl group substituted with 1 to 3 substituents, an aryl group having 6 to 14 carbon atoms, and a 6 to 6 carbon atom substituted with 1 to 5 substituents selected from the group ⁇ below.
  • Group ⁇ an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, a carboxyl group, an amino group, a carbon number of 1 to 6 Mono or dialkylamino group, heterocyclic group, substituted with 1 to 5 substituents selected from the following ⁇ groups, CH s O (CH 2 CH a O) n A group (in the formula, n is an integer of 1 to 6), and a halogen atom.
  • Group ⁇ alkyl group having 1 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, halogen atom, amino group, and 1 or 2 alkyl groups having 1 to 6 carbon atoms or carbon An amino group substituted by an alkylcarbon group having 1 to 6 carbon atoms; and an alkyl group having 1 to 6 carbon atoms substituted by an alkylcarbon group having 1 to 6 carbon atoms.
  • alkyl group having 1 to 20 carbon atoms or the “alkyl group having 1 to 6 carbon atoms” such as R 9 include, for example, methyl, ethyl, ⁇ -propyl, isopropyl, ⁇ -butyl, chinole , Isoptinole, s-butynole, tert-butylinole, n-pentinole, isopene Butyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, n-xyl, isohexynole, 4-methylpentinole, 3-methylinopentenole, 2-methylinopentenole, 1-methylpentyl, 3-methylpentyl, 3,3-dimethylbutyl , 2,2-Dimethylbutyl, 1,1-Dimethylbutyl, 1,2-Dimethylbutyl, 1,3-Dimethynolebutynole, 2,3-Dimethylbut
  • Examples of the “3- to 8-membered cycloalkyl group” such as R 9 include cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl group, and preferably cyclopropyl or cyclobutyl. Group.
  • the "6 to 1 4 Ariru group atoms" such as the R 9, for example, phenyl, Indeyuru, naphthyl, Fuenansureniru, anthracenyl, and the like, preferably, Hue - a le group. '
  • heterocyclic group such as R s is a 5- to 7-membered heterocyclic group containing 1 to 3 sulfur atoms, oxygen atoms and / or nitrogen atoms.
  • Arophoryl ring such as an aromatic heterocyclic ring such as an imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, triazolyl, tetrazolyl, thiadiazolyl, villar, pyridyl, pyridazinyl, pyrimidinyl, pyrazuryl, and the like.
  • Examples of the “aralkyl group having 7 to 15 carbon atoms” such as R 9 include, for example, benzyl, ⁇ -naphthylmethyl, ⁇ -naphthylmethyl, indelmethyl, phenanthrenylmethyl, anthracelmethyl, diphenylmethyl, Triphenyl methyl, 1-phenylene / le, 2-phenylene / le, 1-naphthyl / lethinole, 2-naphthinolethine, 1-phenylpropyl, 2-phenylpropyl, 3-phenyl pill, 1na Futylpropione; 2-naphthinolepropyl, 3-naphthylpropinole, 1-fuurbutinore, 2-fueninolebutinole, 3-fueninolebutinole, 4-fueninolebutinole, 1-naphtinoleptinole, 2 naphthin
  • Examples of the “arylalkyl group having 8 to 16 carbon atoms” such as R 9 include a styryl group and a 2-naphthylbier group. A styryl group is preferable.
  • Examples of the “halogen atom” such as R 3 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, preferably a fluorine or chlorine atom, and more preferably a fluorine atom.
  • Examples of the “oxodioxolenylmethyl group” in the above ⁇ group include (5-phenyl-2-oxo-1,3-dioxolen-1-4-yl) methinole and [5- (4-methylphenylphenyl) 1) 2-oxo-1, 3-dioxolen-4-yl] methyl, [5-1 (4-methoxyphenyl) -2-oxo-1,3_dioxolen-4-yl] methyl, [5- ( 4 monofluorophenyl) 1 2-oxo-1 1, 3 _ ⁇ 1 4-yl] Mechinore, [5- (4-cloth fenole)-2-oxo-1,3-dioxolene 4-inole] Mechinore, (2-oxo_1,3-dioxolene 4-4-2 Methyl), (5-methyl-1-oxo-1,3-dioxolen 41-yl) methyl, (5
  • R 5 and R 6 whether each showing a is good not benzene ring which may have a connexion substituents together with the carbon to which they are attached connexion substitution such together with the carbon to which respectively R 6 and R 7 are bonded
  • the substituent is , A halogen atom, a cyano group, a nitro group, a group represented by the formula R 1Q — X 3 (wherein R 1Q is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, and 1 An alkyl group having 1 to 6 carbon atoms, a 3- to 8-membered cycloalkyl group, a 3- to 8-membered cycloalkyl group substituted by 1 to 3 with a substituent selected from the following ⁇ group, Aryl group having 6 to 14 carbon atoms
  • R 13 is, water atom, 1 ⁇ with substituents selected alkyl group of 1 to 6 carbon atoms, from the following ⁇ group 3 to 8-substituted alkyl group having 1 to 6 carbon atoms, 3- to 8-membered cycloalkyl group, 3- to 8-membered cycloalkyl group substituted by 1 to 3 with a substituent selected from the following ⁇ group
  • Examples of the monoalkylamino group substituted with an alkyl group having 1 to 6 carbon atoms such as group ⁇ include methylamino, ethylamino, ⁇ -propylamino, isopropylamino, ⁇ _butylamino, isopropylamino, s-butylamino, tert-butylamino, n-pentylamino, isopentylamino, 2-methylbutylamino, neopentylamino, 1-ethylpropylamino, n-hexylamino, isohexylamino, 4-methylpentylamino, 3-methyl Pentylamino, .2-Methylpentylamino, 1-methylpentylamino, 3,3-dimethylbutylamino, 2,2-dimethylbutylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino Lamino
  • dialkylamino group substituted with an alkyl group having 1 to 6 carbon atoms, such as group ⁇ examples include, for example, dimethinolemino, ethylmethylamino, getylamino, dipropylamino, diisopropylamino, dibutylamino, diisoamino.
  • Ri is an unsubstituted poly group, an unsubstituted pyridyl group, or an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, 1 to 6 substituted alkyl group having 1 to 6 carbon atoms, alkylcarbonyl group having 1 to 6 carbon atoms, hydroxyl group, halogen atom, nitro group, cyano group, aminocarbonyl group, alkyl group having 1 to 6 carbon atoms Substituted with 1 to 2 carbon atoms, substituted with 1 to 6 carbon atoms, alkyl monocarbonylamino group, substituted with 1 to 6 carbon atoms, and substituted with 1 to 3 carbon atoms.
  • R 1 is an alkyl group having 1 to 6 carbon atoms, an alkyl-oxy group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with 1 to 3 halogen atoms, carbon A compound which is a phenyl group or a pyridyl group, which is substituted by 1 to 6 alkyl monocarbonyl groups, 1 halogen atom or an amino carbonyl group substituted by 1 alkyl group having 1 to 6 carbon atoms,
  • R 1 is a fuel group or a pyridyl group, i-substituted with a methyl group, a methoxy group, a trifluoromethyl group, a methylcarbol group, a halogen atom or a methylaminocarbonyl group,
  • R 2 is a hydrogen atom, an alkyl-carbonyl group having 1 to 6 carbon atoms, an alkyl-carbonyl group having 1 to 6 carbon atoms and 1 to 3 substituted by a halogen atom or / and an amino group.
  • R 2 is alkyl of 1 to 6 carbon atoms - Karuboeru group, halogen atoms and / or Amino 1-3 substituted alkyl one Karuboeru group having 1 to 6 carbon by a group, having 6 to carbon atoms 1 4 aryl-carboyl groups, 6 to 14 carbon atoms substituted with 1 to 6 alkyloxy groups, aryl-carbonyl group, 1 to 6 carbon atoms alkyloxycarbonyl group An aminocarboyl group substituted with 1 to 6 alkyl groups, an alkylcarboyl group having 1 to 6 carbon atoms substituted with an alkyloxy group having 1 to 6 carbon atoms, 20 alkylcarbonylcarbonylamino-C 1-6 alkyl-carboyl group, C 1-C 6 anoalkyl-carboeroxy-C 1-6 alkyl-carboenyl group, or carbon Numbers 1 to 6 1 or 2-substituted Amino one-carbon number of
  • R 2 is a hydrogen atom, a methyl group, E chill carbonyl group, isopropyl group, triflate Ruo Russia methyl mosquito Ruboeru group, phenylpropyl group, 4-main Toshikifue two Rukaruboenore group, main Tokishikanorepo two Nore group, t-toxoxy canolebonyl group, dimethylaminocarboyl group, aminomethylcarbonyl group, 2-methylpropyloxycarbel group, methoxymethylcarbonyl group, acetylaminomethylcarbonyl group, acetoxymethylenecarbonyl group, A compound that is a methylaminomethylene carboxy group or a dimethylaminomethylenecarbonyl group,
  • R 2 is a methyl carboxymethyl El group, Echirukarubo - group, I isopropyl carbonitrile El group, triflate Bruno Leo Lome Chile carbonyl group, Hue - Rukarupo - Honoré group, 4-main tosyl Kifue two Rukanorebo - group, Methoxycarbonyl group, t-butoxycarbonyl group, dimethylaminocarboyl group, aminomethylcarboyl group, 2-methylpropyloxycarbonyl group, methoxymethylcarboyl group, acetylaminoaminocarbol Group, acetoxymethylene group, olebonyl group, methylaminomethylene Or a compound that is a dimethylaminomethylenecarbonyl group,
  • R 2 is a hydrogen atom, a methyl group, E chill carbonyl group, isopropyl group, main butoxycarbonyl group, dimethyl ⁇ amino carbonitrile El group, an amino methyl group, 2-methylpropyl O butoxycarbonyl A methoxymethylcarboyl group, an acetylaminomethylcarbonyl group, an acetyloxymethylene group, a methylaminomethylenecarbonyl group, or a dimethylaminomethylenecarboyl group,
  • R 2 is methylcarbonyl, ethylcarbonyl, isopropylcarbonyl, methoxycarbon, dimethylaminocarbon, aminomethylcarbonyl, 2-methylpropyloxycarbonyl, methoxy
  • R 2 is a hydrogen atom, a methylcarbyl group, an aminomethylcarbol group, a 2-methylpropyloxycarbonyl group, a methoxymethylcarbol group, an acetylmethylaminomethylcarbonyl group, an acetoxy Compounds that are a methylene carbell group, a methylaminomethylene carbyl group, or a dimethylaminomethylene carbyl group
  • R 2 is a methylcarbonyl group, an aminomethylcarboyl group, a 2-methylpropylpyroxycarbonyl group, a methoxymethylcarbonyl group, an acetylaminomethylcarbyl group, an acetoxymethylenecarboel Or a compound that is a methylaminomethylenecarbonyl group or a dimethylaminomethylenecarboyl group
  • R 3 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms
  • R 3 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
  • R 4 is to 1 to 6 carbon atoms alkyl group, 3 to 8-membered cycloalkyl group, 1 to 3-substituted having 1 to 6 carbon alkyl group having a carbon halogen atom, having 1 ⁇ optimum carbon
  • R 4 is methyl, ethyl, propyl, 1-methylethyl, 1-methylpropyl, cyclobutyl, trifluoromethyl, methoxymethyl, methoxycarboyl
  • R 4 is an alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms substituted with 1 to 3 halogen atoms or an aminocarbonyl group,
  • R 5 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a hydroxyl group, an amino group, or a carbon number substituted with 1 to 3 halogen atoms.
  • R 5 is an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a hydroxyl group, an amino group, or a carbon number of 1 to 6 substituted with 1 to 3 halogen atoms.
  • R s is a hydrogen atom, 1 to 4 alkyl groups having a carbon number, having 1 to 4 Arukiruokishi group carbon, a hydroxyl group, an amino group, or 1 to 3 substituted carbon with a halogen atom
  • R s is a hydrogen atom, 1 to 4 alkyl groups having a carbon number, having 1 to 4 Arukiruokishi group carbon, a hydroxyl group, an amino group, or 1 to 3 substituted carbon with a halogen atom
  • R 5 is an alkyl group having 1 to 4 carbon atoms, an alkyloxy group having 1 to 4 carbon atoms, a hydroxyl group, an amino group, or a carbon number of 1 to 3 substituted with 1 to 3 halogen atoms.
  • R 5 is a hydrogen atom, a methynole group, a methoxy group, a hydroxyl group, an amino group or a trifluoromethylcarbonylamino group
  • (16-2) a compound wherein R 5 is a methyl group, a methoxy group, a hydroxyl group, an amino group or a trifluoromethylcarbonylamino group;
  • (17-1) a compound wherein R 5 is a hydrogen atom, a methyl group, a methoxy group, a hydroxyl group or an amino group
  • (17-2) a compound wherein R 5 is a hydrogen atom, a methyl group, a methoxy group, a hydroxyl group or an amino group
  • R 7 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a halogen atom, an alkyl group having 1 to 6 carbon atoms substituted by 1 to 3 carbon atoms or an amino group ,
  • R 7 is an alkyl group having 1 to 6 carbon atoms, a halogen atom, a halogen atom, and an alkyl group having 1 to 6 carbon atoms or an amino group substituted with 1 to 3;
  • R 7 is a hydrogen atom, a methyl group, a chlorine atom, a bromine atom, a trifluoromethyl group or an amino group
  • R 1 is selected from the above (1) to (3)
  • R 2 is selected from the above (4) to (6)
  • R 3 is selected from the above (7) to (9)
  • R 4 is selected.
  • R 5 is selected from the above (14) to (17)
  • R 6 is selected from the above (18) to (21)
  • R 7 is the above (22)
  • R 8 is selected from the above (25) to (27)
  • X 1 is selected from the above (28) to (29).
  • the partial structural formula of the compound of the present invention has the general formula
  • the partial structural formula of the compound of the present invention has the general formula
  • the partial structural formula of the compound of the present invention has the general formula
  • the “pharmacologically acceptable salt” means the compound (1) of the present invention, which can be converted into a salt, and refers to a salt thereof.
  • a salt is preferably a sodium salt or potassium salt
  • Alkaline metal salts such as lithium salts, alkaline earth metal salts such as calcium salts, magnesium salts, aluminum salts, iron salts, zinc salts, copper salts, nickel salts, metal salts such as cobalt salts; ammonium salts Inorganic salts, t-octylamine salts, dibenzylamine salts, morpholine salts, glucosamine salts, phenylglycine alkyl ester salts, ethylenediamine salts, N-methyldalcamine salts, guanidin salts, getylamine salts, triethylamine salts, dicyclohexylamine salts , N, N'-dibenzylethylene diamine salt, black mouth pro-force salt, pro-force salt,
  • Inorganic acid salts lower alkanesulfonic acid salts such as methanesulfonic acid salt, trifluoromethanesulfonic acid salt, ethanesulfonic acid salt, arylsulfonic acid salts such as benzenesulfonic acid salt, p-toluenesulfonic acid salt, and acetic acid , Malic acid, fumarate, succinate, citrate, tartrate, oxalate, maleate, and other organic acid salts; and glycin, lysine, algin, and orutin salts; Amino acid salts such as glutamate and aspartate can be mentioned.
  • lower alkanesulfonic acid salts such as methanesulfonic acid salt, trifluoromethanesulfonic acid salt, ethanesulfonic acid salt, arylsulfonic acid salts such as benzenesulfonic acid salt, p-toluene
  • the compound (1) of the present invention may absorb water and become adsorbed water or form a hydrate when left in the air, and such salts are also included in the present invention. Is done.
  • the compound (1) of the present invention may absorb some other solvent to form a solvate, and such salts are also included in the present invention.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Pr represents a propyl group
  • Bu represents a butyl group
  • tBu represents a t-butyl group
  • cPr represents a cycle.
  • Propyl group, cBu is cyclobutyl group
  • cHx is cyclohexyl group
  • Naph naphthyl group
  • Ph is fuel group
  • Pyr is pyridyl group
  • Fur is furyl group.
  • T hi represents a chel group
  • Mor represents a morpholino group.
  • 4 84 and 48 5 is: More preferred are 3, 16, 18, 18, 27, 29, 56, 57, 59, 128, 144, 144, 144, 146, 147, 448, 449, 450, 445 45 2, 453, 454, 455, 456, 457, 458, 449, 460, 461, 462, 463, 464 , 465, 466, 467, 468, 469, 470, 47 1, 472, 473, 474, 475, 476, 471, 478, 479, 480, 48 1 48 2, 483, 484 and 485.
  • the preferred ones are lb, 2b, 3b, 4b, 5b, 6b, 1Ob, lib, 12b, 13 b, 14b, 15b, 16b, 17b, 19b, 2Ob, 21b, 22b, 23b, 24b, 25b, 27b, 28b, 29b, 3Ob , 31b, 32b, 33b, 34b, 35b, 37b, 38b and 39b, and more preferred are 2b, 3b, 5b, 10b, 12b, 13 b, 14b, 16b, 21b, 22b, 30b, 3lb and 32b.
  • the preferred ones are ld, 2 d, 3 d, 4 d, 5 d, 6 d, 10 d, lld, 12 d, 1 3d, 14d, 15d, 16d, 17d, 19d, 20d, 21d, 22d, 23d, 24d, 25d, 27d, 28d, 29 d, 30 d, 31 d, 32 d, 33 d, 34 d, 35 d, 37 d, 38 d and 39 d, and more preferred are., 2 d, 3 d, 5 d, 10 d, 12 d, 13 d, 14 d, 16 d, 21 d, 22 d, 30 d, 3 Id and 32 d.
  • Specific examples of the compound (1) of the present invention include a combination obtained by arbitrarily selecting one from Table 1 and optionally selecting one from Tables 2, 3, 4, and 5. , Specifically, for example, 1-la, 1-2a, 1-7a, 1-21a, l-33a, 1-39a, 2--15a, 3-la, 3-2a, 3_3a, 3_4a, 3-5a, 3-6a, 3_10a, 3-11a, 3-1-2a3-13a, 3-14a, Three

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Abstract

L'invention concerne de nouveaux dérivés d'imidazopyridine présentant une importante activité antitumorale, comprenant les composés représentés par la formule générale (1) ou des sels pharmaceutiquement acceptables de ceux-ci. R1 représente le phényle substitué, un hétérocycle substitué etc., R2 représente l'hydrogènes, l'acyle aliphatique etc., R?3, R4, R5. R6, R7 et R8¿ représentent chacun l'hydrogène, alkyle, halogéno etc, et X1 représente O, S etc.
PCT/JP2001/009258 2000-10-24 2001-10-22 Derives d'imidazopyridine Ceased WO2002034748A1 (fr)

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AU2001295992A AU2001295992A1 (en) 2000-10-24 2001-10-22 Imidazopyridine derivatives

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JP2000-324043 2000-10-24
JP2000-392331 2000-12-25
JP2000392331 2000-12-25

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Cited By (45)

* Cited by examiner, † Cited by third party
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WO2003015773A2 (fr) 2001-08-13 2003-02-27 Janssen Pharmaceutica N.V. Derives de thiazolyl 2-amino-4,5-trisubstitue
EP1277754A4 (fr) * 2000-04-27 2003-06-04 Yamanouchi Pharma Co Ltd Derives d'imidazopyridine
DE10247271A1 (de) * 2002-10-10 2004-08-26 Grünenthal GmbH Substituierte C-Imidazo[1,2-a]pyridin-3-yle
WO2006050351A3 (fr) * 2004-10-28 2007-02-22 Irm Llc Composes et compositions servant de modulateurs de la voie de signalisation hedgehog
US7563797B2 (en) 2006-08-28 2009-07-21 Forest Laboratories Holding Limited Substituted imidazo(1,2-A)pyrimidines and imidazo(1,2-A) pyridines as cannabinoid receptor ligands
US20110052527A1 (en) * 2007-06-26 2011-03-03 Gilead Sciences, Inc. Imidazopyridinyl thiazolyl histone deacetylase inhibitors
US8030327B2 (en) 2004-11-08 2011-10-04 Mds K.K. Fused imidazole derivative
US8071614B2 (en) 2007-10-12 2011-12-06 Astex Therapeutics Limited Bicyclic heterocyclic compounds as protein tyrosine kinase inhibitors
US8076354B2 (en) 2007-10-12 2011-12-13 Astex Therapeutics Limited Bicyclic heterocyclic compounds as protein tyrosine kinase inhibitors
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